data_Compound_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 N2 O2' _chemical_formula_sum 'C26 H20 N2 O2' _chemical_formula_weight 392.44 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.691(2) _cell_length_b 19.642(4) _cell_length_c 7.719(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.123(2) _cell_angle_gamma 90.00 _cell_volume 1013.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6471 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 28.4 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\p and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6471 _diffrn_reflns_av_R_equivalents 0.0724 _diffrn_reflns_av_sigmaI/netI 0.0957 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.40 _reflns_number_total 3803 _reflns_number_gt 2439 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 3' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1545P)^2^+0.6144P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_number_reflns 3803 _refine_ls_number_parameters 271 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1367 _refine_ls_R_factor_gt 0.0936 _refine_ls_wR_factor_ref 0.2105 _refine_ls_wR_factor_gt 0.2315 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 N1 N 0.2605(7) 0.7674(2) 0.6697(6) 0.0360(11) Uani 1 1 d . . . O1 O -0.0348(6) 0.7676(2) 0.8197(5) 0.0419(10) Uani 1 1 d . . . O2 O 0.1830(7) 0.3367(2) 0.9160(6) 0.0510(12) Uani 1 1 d . . . H2 H 0.1027 0.3197 0.9811 0.076 Uiso 1 1 calc R . . N2 N 0.3325(7) 0.6559(2) 0.6668(6) 0.0353(11) Uani 1 1 d . . . C2 C 0.1569(9) 0.6654(3) 0.7531(7) 0.0351(12) Uani 1 1 d . . . C4 C 0.0470(9) 0.6163(3) 0.8316(7) 0.0364(13) Uani 1 1 d . . . H4 H -0.0675 0.6319 0.8837 0.044 Uiso 1 1 calc R . . C1 C 0.3932(9) 0.7157(3) 0.6196(7) 0.0350(12) Uani 1 1 d . . . C21 C 0.2878(9) 0.8395(3) 0.6508(7) 0.0392(13) Uani 1 1 d . . . C3 C 0.1068(8) 0.7383(3) 0.7569(7) 0.0350(12) Uani 1 1 d . . . C9 C -0.0124(9) 0.4362(3) 0.9754(8) 0.0418(14) Uani 1 1 d . . . H9 H -0.0968 0.4118 1.0456 0.050 Uiso 1 1 calc R . . C11 C 0.5645(9) 0.7309(3) 0.5213(8) 0.0389(13) Uani 1 1 d . . . H11 H 0.5801 0.7751 0.4808 0.047 Uiso 1 1 calc R . . C17 C 1.4042(9) 0.7520(4) 0.1004(8) 0.0450(15) Uani 1 1 d . . . H17 H 1.4348 0.7966 0.0702 0.054 Uiso 1 1 calc R . . C16 C 1.2403(8) 0.7393(3) 0.1929(7) 0.0370(13) Uani 1 1 d . . . H16 H 1.1587 0.7752 0.2241 0.044 Uiso 1 1 calc R . . C10 C -0.0426(9) 0.5049(3) 0.9480(8) 0.0444(15) Uani 1 1 d . . . H10 H -0.1499 0.5258 0.9998 0.053 Uiso 1 1 calc R . . C26 C 0.4644(10) 0.8688(3) 0.7210(8) 0.0449(15) Uani 1 1 d . . . H26 H 0.5601 0.8418 0.7781 0.054 Uiso 1 1 calc R . . C22 C 0.1483(10) 0.8777(3) 0.5653(8) 0.0486(15) Uani 1 1 d . . . H22 H 0.0324 0.8578 0.5183 0.058 Uiso 1 1 calc R . . C20 C 1.3163(9) 0.6205(3) 0.1963(8) 0.0424(14) Uani 1 1 d . . . H20 H 1.2885 0.5760 0.2292 0.051 Uiso 1 1 calc R . . C15 C 1.1912(8) 0.6726(3) 0.2428(7) 0.0381(13) Uani 1 1 d . . . C6 C 0.2375(9) 0.5097(3) 0.7658(8) 0.0413(14) Uani 1 1 d . . . H6 H 0.3214 0.5336 0.6941 0.050 Uiso 1 1 calc R . . C25 C 0.4949(11) 0.9372(3) 0.7050(9) 0.0520(16) Uani 1 1 d . . . H25 H 0.6098 0.9572 0.7538 0.062 Uiso 1 1 calc R . . C19 C 1.4857(10) 0.6340(4) 0.0994(8) 0.0489(17) Uani 1 1 d . . . H19 H 1.5698 0.5986 0.0688 0.059 Uiso 1 1 calc R . . C5 C 0.0812(9) 0.5445(3) 0.8458(7) 0.0354(12) Uani 1 1 d . . . C14 C 1.0162(9) 0.6578(3) 0.3439(7) 0.0368(12) Uani 1 1 d . . . H14 H 1.0047 0.6135 0.3847 0.044 Uiso 1 1 calc R . . C12 C 0.7019(9) 0.6851(3) 0.4851(8) 0.0378(13) Uani 1 1 d . . . H12 H 0.6880 0.6411 0.5271 0.045 Uiso 1 1 calc R . . C8 C 0.1442(9) 0.4040(3) 0.8977(7) 0.0393(13) Uani 1 1 d . . . C13 C 0.8717(9) 0.7006(3) 0.3838(7) 0.0369(13) Uani 1 1 d . . . H13 H 0.8813 0.7449 0.3422 0.044 Uiso 1 1 calc R . . C18 C 1.5266(9) 0.6993(4) 0.0503(8) 0.0479(16) Uani 1 1 d . . . H18 H 1.6364 0.7083 -0.0166 0.058 Uiso 1 1 calc R . . C23 C 0.1809(12) 0.9477(4) 0.5485(9) 0.0571(18) Uani 1 1 d . . . H23 H 0.0849 0.9747 0.4917 0.069 Uiso 1 1 calc R . . C24 C 0.3538(14) 0.9770(4) 0.6154(10) 0.064(2) Uani 1 1 d . . . H24 H 0.3762 1.0233 0.6008 0.077 Uiso 1 1 calc R . . C7 C 0.2678(9) 0.4414(3) 0.7918(9) 0.0463(15) Uani 1 1 d . . . H7 H 0.3724 0.4197 0.7381 0.056 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 N1 0.044(3) 0.024(2) 0.040(2) -0.0013(19) 0.005(2) -0.001(2) O1 0.047(2) 0.032(2) 0.047(2) -0.0058(17) 0.0099(18) 0.006(2) O2 0.059(3) 0.025(2) 0.070(3) 0.004(2) 0.018(2) -0.004(2) N2 0.041(3) 0.025(3) 0.040(2) -0.0025(19) 0.009(2) 0.000(2) C2 0.041(3) 0.032(3) 0.031(3) -0.003(2) -0.001(2) -0.006(3) C4 0.036(3) 0.034(3) 0.040(3) -0.001(2) 0.011(2) 0.006(3) C1 0.048(3) 0.023(3) 0.035(3) -0.003(2) 0.004(2) 0.001(3) C21 0.046(3) 0.028(3) 0.045(3) 0.005(2) 0.013(3) -0.002(3) C3 0.029(3) 0.037(3) 0.039(3) -0.007(2) 0.007(2) -0.005(2) C9 0.043(3) 0.030(3) 0.053(3) 0.008(3) 0.018(3) -0.002(3) C11 0.046(3) 0.028(3) 0.043(3) 0.004(2) 0.005(3) -0.001(3) C17 0.038(3) 0.051(4) 0.046(3) 0.004(3) 0.007(2) 0.000(3) C16 0.035(3) 0.033(3) 0.042(3) 0.000(2) 0.001(2) 0.002(2) C10 0.042(3) 0.032(3) 0.060(4) 0.003(3) 0.022(3) -0.002(3) C26 0.051(4) 0.029(3) 0.055(3) 0.005(3) 0.002(3) -0.001(3) C22 0.054(4) 0.039(4) 0.052(3) -0.006(3) 0.000(3) 0.001(3) C20 0.040(3) 0.038(4) 0.051(3) 0.006(3) 0.008(3) -0.001(3) C15 0.035(3) 0.040(4) 0.039(3) 0.004(2) 0.001(2) 0.005(3) C6 0.043(3) 0.031(3) 0.051(3) 0.007(2) 0.018(3) -0.006(3) C25 0.063(4) 0.028(3) 0.064(4) 0.003(3) -0.008(3) -0.011(3) C19 0.045(3) 0.052(4) 0.050(3) -0.016(3) 0.007(3) 0.015(3) C5 0.041(3) 0.028(3) 0.038(3) 0.002(2) 0.008(2) 0.000(2) C14 0.040(3) 0.031(3) 0.040(3) 0.000(2) 0.003(2) -0.006(3) C12 0.041(3) 0.031(3) 0.041(3) 0.001(2) 0.002(2) -0.012(3) C8 0.040(3) 0.027(3) 0.051(3) 0.000(3) 0.007(3) -0.006(3) C13 0.041(3) 0.034(3) 0.035(3) 0.000(2) 0.001(2) -0.005(3) C18 0.036(3) 0.065(5) 0.044(3) 0.002(3) 0.009(3) -0.001(3) C23 0.078(5) 0.036(4) 0.056(4) 0.007(3) -0.008(4) 0.011(4) C24 0.100(6) 0.027(3) 0.065(4) 0.006(3) -0.006(4) -0.008(4) C7 0.040(3) 0.035(4) 0.065(4) 0.002(3) 0.020(3) 0.004(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 N1 C3 1.375(7) . ? N1 C1 1.412(7) . ? N1 C21 1.437(7) . ? O1 C3 1.224(6) . ? O2 C8 1.354(7) . ? O2 H2 0.8200 . ? N2 C1 1.299(7) . ? N2 C2 1.385(7) . ? C2 C4 1.369(8) . ? C2 C3 1.471(8) . ? C4 C5 1.432(8) . ? C4 H4 0.9300 . ? C1 C11 1.429(8) . ? C21 C22 1.351(9) . ? C21 C26 1.405(9) . ? C9 C8 1.380(8) . ? C9 C10 1.380(9) . ? C9 H9 0.9300 . ? C11 C12 1.323(8) . ? C11 H11 0.9300 . ? C17 C16 1.354(8) . ? C17 C18 1.384(10) . ? C17 H17 0.9300 . ? C16 C15 1.408(8) . ? C16 H16 0.9300 . ? C10 C5 1.400(7) . ? C10 H10 0.9300 . ? C26 C25 1.366(9) . ? C26 H26 0.9300 . ? C22 C23 1.399(10) . ? C22 H22 0.9300 . ? C20 C15 1.378(9) . ? C20 C19 1.406(9) . ? C20 H20 0.9300 . ? C15 C14 1.460(8) . ? C6 C7 1.372(9) . ? C6 C5 1.410(8) . ? C6 H6 0.9300 . ? C25 C24 1.389(11) . ? C25 H25 0.9300 . ? C19 C18 1.369(10) . ? C19 H19 0.9300 . ? C14 C13 1.327(8) . ? C14 H14 0.9300 . ? C12 C13 1.435(7) . ? C12 H12 0.9300 . ? C8 C7 1.394(8) . ? C13 H13 0.9300 . ? C18 H18 0.9300 . ? C23 C24 1.375(12) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C7 H7 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C1 108.9(5) . . ? C3 N1 C21 124.0(5) . . ? C1 N1 C21 126.7(5) . . ? C8 O2 H2 109.5 . . ? C1 N2 C2 107.0(5) . . ? C4 C2 N2 126.7(5) . . ? C4 C2 C3 123.4(5) . . ? N2 C2 C3 109.8(5) . . ? C2 C4 C5 129.9(5) . . ? C2 C4 H4 115.0 . . ? C5 C4 H4 115.0 . . ? N2 C1 N1 111.5(5) . . ? N2 C1 C11 127.1(5) . . ? N1 C1 C11 121.3(5) . . ? C22 C21 C26 121.1(6) . . ? C22 C21 N1 120.6(6) . . ? C26 C21 N1 118.2(5) . . ? O1 C3 N1 127.0(5) . . ? O1 C3 C2 130.3(5) . . ? N1 C3 C2 102.7(4) . . ? C8 C9 C10 119.5(5) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C12 C11 C1 123.2(5) . . ? C12 C11 H11 118.4 . . ? C1 C11 H11 118.4 . . ? C16 C17 C18 120.5(6) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C16 C15 121.2(5) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C9 C10 C5 122.9(5) . . ? C9 C10 H10 118.6 . . ? C5 C10 H10 118.6 . . ? C25 C26 C21 119.6(6) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? C21 C22 C23 119.0(7) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C15 C20 C19 120.5(6) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C15 C16 118.0(5) . . ? C20 C15 C14 119.9(6) . . ? C16 C15 C14 122.1(5) . . ? C7 C6 C5 121.2(5) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C26 C25 C24 119.8(7) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C18 C19 C20 119.8(6) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C10 C5 C6 116.2(5) . . ? C10 C5 C4 119.6(5) . . ? C6 C5 C4 124.2(5) . . ? C13 C14 C15 127.2(6) . . ? C13 C14 H14 116.4 . . ? C15 C14 H14 116.4 . . ? C11 C12 C13 122.8(5) . . ? C11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? O2 C8 C9 123.3(5) . . ? O2 C8 C7 117.4(5) . . ? C9 C8 C7 119.3(6) . . ? C14 C13 C12 126.2(5) . . ? C14 C13 H13 116.9 . . ? C12 C13 H13 116.9 . . ? C19 C18 C17 119.8(6) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C24 C23 C22 120.5(7) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 119.9(7) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C6 C7 C8 120.9(5) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N2 C2 C4 -176.8(6) . . . . ? C1 N2 C2 C3 0.4(6) . . . . ? N2 C2 C4 C5 0.0(10) . . . . ? C3 C2 C4 C5 -176.9(6) . . . . ? C2 N2 C1 N1 -0.8(6) . . . . ? C2 N2 C1 C11 -177.6(5) . . . . ? C3 N1 C1 N2 1.0(6) . . . . ? C21 N1 C1 N2 174.9(5) . . . . ? C3 N1 C1 C11 177.9(5) . . . . ? C21 N1 C1 C11 -8.1(8) . . . . ? C3 N1 C21 C22 -62.4(8) . . . . ? C1 N1 C21 C22 124.6(6) . . . . ? C3 N1 C21 C26 118.7(6) . . . . ? C1 N1 C21 C26 -54.4(7) . . . . ? C1 N1 C3 O1 179.7(5) . . . . ? C21 N1 C3 O1 5.5(9) . . . . ? C1 N1 C3 C2 -0.7(6) . . . . ? C21 N1 C3 C2 -174.8(5) . . . . ? C4 C2 C3 O1 -2.9(10) . . . . ? N2 C2 C3 O1 179.8(6) . . . . ? C4 C2 C3 N1 177.5(5) . . . . ? N2 C2 C3 N1 0.2(6) . . . . ? N2 C1 C11 C12 -9.8(9) . . . . ? N1 C1 C11 C12 173.8(5) . . . . ? C18 C17 C16 C15 0.9(9) . . . . ? C8 C9 C10 C5 -0.9(10) . . . . ? C22 C21 C26 C25 1.0(9) . . . . ? N1 C21 C26 C25 179.9(6) . . . . ? C26 C21 C22 C23 -0.6(9) . . . . ? N1 C21 C22 C23 -179.5(6) . . . . ? C19 C20 C15 C16 -1.0(9) . . . . ? C19 C20 C15 C14 -179.8(6) . . . . ? C17 C16 C15 C20 0.7(8) . . . . ? C17 C16 C15 C14 179.5(5) . . . . ? C21 C26 C25 C24 -1.7(10) . . . . ? C15 C20 C19 C18 -0.2(9) . . . . ? C9 C10 C5 C6 2.0(9) . . . . ? C9 C10 C5 C4 -176.4(6) . . . . ? C7 C6 C5 C10 -1.7(9) . . . . ? C7 C6 C5 C4 176.7(6) . . . . ? C2 C4 C5 C10 173.7(6) . . . . ? C2 C4 C5 C6 -4.7(10) . . . . ? C20 C15 C14 C13 -172.8(6) . . . . ? C16 C15 C14 C13 8.5(9) . . . . ? C1 C11 C12 C13 178.9(5) . . . . ? C10 C9 C8 O2 -179.2(6) . . . . ? C10 C9 C8 C7 -0.6(9) . . . . ? C15 C14 C13 C12 -179.2(5) . . . . ? C11 C12 C13 C14 179.2(6) . . . . ? C20 C19 C18 C17 1.8(10) . . . . ? C16 C17 C18 C19 -2.2(10) . . . . ? C21 C22 C23 C24 1.1(11) . . . . ? C22 C23 C24 C25 -1.9(12) . . . . ? C26 C25 C24 C23 2.2(11) . . . . ? C5 C6 C7 C8 0.3(10) . . . . ? O2 C8 C7 C6 179.6(6) . . . . ? C9 C8 C7 C6 0.8(10) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.400 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.106 #==========# data_Compound_II _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 N2 O2' _chemical_formula_sum 'C22 H20 N2 O2' _chemical_formula_weight 344.40 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P2yn 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 14.121(5) _cell_length_b 10.361(4) _cell_length_c 14.130(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.632(7) _cell_angle_gamma 90.00 _cell_volume 1831.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4499 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.3 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\p and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11792 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 28.34 _reflns_number_total 4499 _reflns_number_gt 1969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 3' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0976P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4499 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.2079 _refine_ls_wR_factor_gt 0.1612 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 O2 O -0.22875(15) -0.2225(2) 0.68989(14) 0.0959(6) Uani 1 1 d . . . O1 O 0.32332(15) 0.26250(18) 1.03849(13) 0.0890(6) Uani 1 1 d . . . N1 N 0.28051(15) 0.34119(18) 0.86956(14) 0.0651(5) Uani 1 1 d . . . N2 N 0.14260(16) 0.21169(18) 0.76549(14) 0.0646(5) Uani 1 1 d . . . C5 C 0.04170(18) 0.0067(2) 0.85228(17) 0.0621(6) Uani 1 1 d . . . C2 C 0.17705(17) 0.1769(2) 0.87181(17) 0.0615(6) Uani 1 1 d . . . C4 C 0.13428(19) 0.0868(2) 0.90947(18) 0.0655(6) Uani 1 1 d . . . H4 H 0.1697 0.0747 0.9831 0.079 Uiso 1 1 calc R . . C1 C 0.20271(19) 0.3079(2) 0.76699(18) 0.0632(6) Uani 1 1 d . . . C8 C -0.1396(2) -0.1509(2) 0.7481(2) 0.0703(7) Uani 1 1 d . . . C11 C 0.19189(19) 0.3746(2) 0.67251(18) 0.0705(7) Uani 1 1 d . . . H11 H 0.2404 0.4394 0.6797 0.085 Uiso 1 1 calc R . . C3 C 0.2685(2) 0.2598(2) 0.94063(19) 0.0687(6) Uani 1 1 d . . . C6 C -0.02840(19) 0.0204(2) 0.74222(18) 0.0706(7) Uani 1 1 d . . . H6 H -0.0149 0.0833 0.7031 0.085 Uiso 1 1 calc R . . C9 C -0.0735(2) -0.1653(3) 0.8564(2) 0.0763(7) Uani 1 1 d . . . H9 H -0.0890 -0.2268 0.8952 0.092 Uiso 1 1 calc R . . C7 C -0.1157(2) -0.0574(3) 0.6923(2) 0.0778(7) Uani 1 1 d . . . H7 H -0.1600 -0.0475 0.6195 0.093 Uiso 1 1 calc R . . C12 C 0.11421(19) 0.3456(2) 0.57536(18) 0.0711(7) Uani 1 1 d . . . H12 H 0.0682 0.2791 0.5713 0.085 Uiso 1 1 calc R . . C15 C -0.01497(19) 0.4235(2) 0.27752(18) 0.0687(6) Uani 1 1 d . . . C14 C 0.0152(2) 0.3709(3) 0.3834(2) 0.0765(7) Uani 1 1 d . . . H14 H -0.0271 0.3033 0.3856 0.092 Uiso 1 1 calc R . . C13 C 0.0943(2) 0.4057(2) 0.47693(18) 0.0717(7) Uani 1 1 d . . . H13 H 0.1390 0.4726 0.4786 0.086 Uiso 1 1 calc R . . C10 C 0.0155(2) -0.0878(2) 0.90638(19) 0.0729(7) Uani 1 1 d . . . H10 H 0.0599 -0.0991 0.9791 0.087 Uiso 1 1 calc R . . C22 C 0.3572(2) 0.4450(3) 0.9004(2) 0.0862(8) Uani 1 1 d . . . H22A H 0.3519 0.4870 0.8375 0.129 Uiso 1 1 calc R . . H22B H 0.4280 0.4108 0.9410 0.129 Uiso 1 1 calc R . . H22C H 0.3428 0.5062 0.9430 0.129 Uiso 1 1 calc R . . C16 C 0.0311(2) 0.5325(3) 0.2587(2) 0.0805(7) Uani 1 1 d . . . H16 H 0.0842 0.5772 0.3157 0.097 Uiso 1 1 calc R . . C20 C -0.0943(2) 0.3614(3) 0.1890(2) 0.0858(8) Uani 1 1 d . . . H20 H -0.1274 0.2891 0.1992 0.103 Uiso 1 1 calc R . . C19 C -0.1249(3) 0.4040(4) 0.0871(2) 0.1006(10) Uani 1 1 d . . . H19 H -0.1772 0.3593 0.0295 0.121 Uiso 1 1 calc R . . C21 C -0.2567(2) -0.3211(3) 0.7426(2) 0.1038(10) Uani 1 1 d . . . H21A H -0.3214 -0.3625 0.6923 0.156 Uiso 1 1 calc R . . H21B H -0.2673 -0.2837 0.7991 0.156 Uiso 1 1 calc R . . H21C H -0.2002 -0.3836 0.7719 0.156 Uiso 1 1 calc R . . C17 C -0.0017(3) 0.5745(3) 0.1553(3) 0.0995(10) Uani 1 1 d . . . H17 H 0.0298 0.6476 0.1438 0.119 Uiso 1 1 calc R . . C18 C -0.0795(3) 0.5110(4) 0.0694(2) 0.1039(10) Uani 1 1 d . . . H18 H -0.1009 0.5405 0.0003 0.125 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 O2 0.0857(14) 0.1138(15) 0.0799(13) 0.0077(11) 0.0315(11) -0.0232(11) O1 0.0947(13) 0.1012(14) 0.0513(11) 0.0007(9) 0.0170(9) -0.0072(10) N1 0.0655(12) 0.0708(12) 0.0529(11) -0.0018(10) 0.0223(10) 0.0000(10) N2 0.0717(13) 0.0704(12) 0.0505(11) 0.0031(9) 0.0274(10) 0.0046(10) C5 0.0698(16) 0.0642(14) 0.0525(13) 0.0037(11) 0.0286(12) 0.0077(12) C2 0.0617(14) 0.0693(15) 0.0503(13) 0.0034(11) 0.0234(11) 0.0098(12) C4 0.0704(15) 0.0719(15) 0.0482(12) 0.0054(11) 0.0225(11) 0.0109(13) C1 0.0660(15) 0.0668(15) 0.0568(14) 0.0012(12) 0.0285(12) 0.0057(12) C8 0.0656(16) 0.0806(17) 0.0657(16) 0.0023(13) 0.0314(13) -0.0014(13) C11 0.0775(17) 0.0742(16) 0.0603(15) 0.0048(12) 0.0325(13) -0.0016(13) C3 0.0713(16) 0.0733(16) 0.0561(15) 0.0002(12) 0.0251(13) 0.0079(13) C6 0.0689(16) 0.0845(17) 0.0586(14) 0.0110(13) 0.0298(13) 0.0011(13) C9 0.0827(18) 0.0792(17) 0.0690(16) 0.0136(13) 0.0370(14) -0.0012(15) C7 0.0728(17) 0.101(2) 0.0558(14) 0.0092(14) 0.0266(13) -0.0037(15) C12 0.0791(17) 0.0760(16) 0.0602(15) 0.0033(12) 0.0339(13) 0.0012(13) C15 0.0759(16) 0.0756(16) 0.0546(14) 0.0008(12) 0.0303(13) 0.0077(13) C14 0.0870(18) 0.0779(17) 0.0646(16) 0.0018(13) 0.0350(14) -0.0069(14) C13 0.0804(17) 0.0756(16) 0.0600(15) 0.0006(12) 0.0333(13) -0.0034(13) C10 0.0838(18) 0.0768(17) 0.0543(14) 0.0098(12) 0.0289(13) 0.0062(14) C22 0.0797(19) 0.0884(19) 0.0809(18) -0.0080(15) 0.0290(15) -0.0155(15) C16 0.0873(18) 0.0886(19) 0.0660(16) 0.0063(14) 0.0359(14) 0.0045(15) C20 0.0850(19) 0.093(2) 0.0692(18) -0.0020(15) 0.0270(15) 0.0057(15) C19 0.097(2) 0.123(3) 0.0598(18) -0.0075(18) 0.0183(15) 0.028(2) C21 0.103(2) 0.104(2) 0.107(2) 0.0033(19) 0.0509(19) -0.0255(18) C17 0.107(2) 0.113(2) 0.086(2) 0.027(2) 0.0517(19) 0.0167(19) C18 0.110(3) 0.135(3) 0.066(2) 0.024(2) 0.0398(19) 0.044(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 O2 C8 1.360(3) . ? O2 C21 1.424(3) . ? O1 C3 1.233(3) . ? N1 C3 1.381(3) . ? N1 C1 1.396(3) . ? N1 C22 1.443(3) . ? N2 C1 1.303(3) . ? N2 C2 1.395(3) . ? C5 C10 1.393(3) . ? C5 C6 1.411(3) . ? C5 C4 1.439(3) . ? C2 C4 1.348(3) . ? C2 C3 1.478(3) . ? C4 H4 0.9300 . ? C1 C11 1.447(3) . ? C8 C9 1.382(3) . ? C8 C7 1.386(3) . ? C11 C12 1.335(3) . ? C11 H11 0.9300 . ? C6 C7 1.364(3) . ? C6 H6 0.9300 . ? C9 C10 1.379(3) . ? C9 H9 0.9300 . ? C7 H7 0.9300 . ? C12 C13 1.428(3) . ? C12 H12 0.9300 . ? C15 C16 1.390(3) . ? C15 C20 1.391(3) . ? C15 C14 1.458(3) . ? C14 C13 1.325(3) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C10 H10 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C16 C17 1.382(4) . ? C16 H16 0.9300 . ? C20 C19 1.370(4) . ? C20 H20 0.9300 . ? C19 C18 1.360(5) . ? C19 H19 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C17 C18 1.370(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 C21 118.6(2) . . ? C3 N1 C1 107.5(2) . . ? C3 N1 C22 124.3(2) . . ? C1 N1 C22 128.0(2) . . ? C1 N2 C2 106.3(2) . . ? C10 C5 C6 116.5(2) . . ? C10 C5 C4 120.0(2) . . ? C6 C5 C4 123.4(2) . . ? C4 C2 N2 127.4(2) . . ? C4 C2 C3 123.9(2) . . ? N2 C2 C3 108.7(2) . . ? C2 C4 C5 129.4(2) . . ? C2 C4 H4 115.3 . . ? C5 C4 H4 115.3 . . ? N2 C1 N1 113.5(2) . . ? N2 C1 C11 124.1(2) . . ? N1 C1 C11 122.4(2) . . ? O2 C8 C9 124.8(2) . . ? O2 C8 C7 116.0(2) . . ? C9 C8 C7 119.2(2) . . ? C12 C11 C1 121.7(2) . . ? C12 C11 H11 119.1 . . ? C1 C11 H11 119.1 . . ? O1 C3 N1 125.2(2) . . ? O1 C3 C2 130.8(2) . . ? N1 C3 C2 103.9(2) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C10 C9 C8 119.5(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C6 C7 C8 121.3(2) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C11 C12 C13 126.9(2) . . ? C11 C12 H12 116.6 . . ? C13 C12 H12 116.6 . . ? C16 C15 C20 117.2(2) . . ? C16 C15 C14 124.1(2) . . ? C20 C15 C14 118.7(3) . . ? C13 C14 C15 129.2(3) . . ? C13 C14 H14 115.4 . . ? C15 C14 H14 115.4 . . ? C14 C13 C12 123.1(3) . . ? C14 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C9 C10 C5 122.6(2) . . ? C9 C10 H10 118.7 . . ? C5 C10 H10 118.7 . . ? N1 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C19 C20 C15 121.8(3) . . ? C19 C20 H20 119.1 . . ? C15 C20 H20 119.1 . . ? C18 C19 C20 120.6(3) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C17 C16 121.5(3) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C19 C18 C17 118.8(3) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N2 C2 C4 175.9(2) . . . . ? C1 N2 C2 C3 -1.8(2) . . . . ? N2 C2 C4 C5 -2.2(4) . . . . ? C3 C2 C4 C5 175.3(2) . . . . ? C10 C5 C4 C2 175.3(2) . . . . ? C6 C5 C4 C2 -6.8(4) . . . . ? C2 N2 C1 N1 1.6(2) . . . . ? C2 N2 C1 C11 -178.9(2) . . . . ? C3 N1 C1 N2 -0.8(3) . . . . ? C22 N1 C1 N2 -177.6(2) . . . . ? C3 N1 C1 C11 179.71(19) . . . . ? C22 N1 C1 C11 2.9(4) . . . . ? C21 O2 C8 C9 -0.9(4) . . . . ? C21 O2 C8 C7 179.3(2) . . . . ? N2 C1 C11 C12 3.5(4) . . . . ? N1 C1 C11 C12 -177.0(2) . . . . ? C1 N1 C3 O1 -179.4(2) . . . . ? C22 N1 C3 O1 -2.4(4) . . . . ? C1 N1 C3 C2 -0.4(2) . . . . ? C22 N1 C3 C2 176.6(2) . . . . ? C4 C2 C3 O1 2.4(4) . . . . ? N2 C2 C3 O1 -179.7(2) . . . . ? C4 C2 C3 N1 -176.5(2) . . . . ? N2 C2 C3 N1 1.4(2) . . . . ? C10 C5 C6 C7 -1.2(3) . . . . ? C4 C5 C6 C7 -179.2(2) . . . . ? O2 C8 C9 C10 179.2(2) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C5 C6 C7 C8 1.1(4) . . . . ? O2 C8 C7 C6 179.9(2) . . . . ? C9 C8 C7 C6 0.0(4) . . . . ? C1 C11 C12 C13 178.8(2) . . . . ? C16 C15 C14 C13 -6.7(4) . . . . ? C20 C15 C14 C13 172.9(3) . . . . ? C15 C14 C13 C12 179.6(2) . . . . ? C11 C12 C13 C14 179.9(3) . . . . ? C8 C9 C10 C5 0.7(4) . . . . ? C6 C5 C10 C9 0.3(3) . . . . ? C4 C5 C10 C9 178.4(2) . . . . ? C20 C15 C16 C17 -0.4(4) . . . . ? C14 C15 C16 C17 179.2(2) . . . . ? C16 C15 C20 C19 1.1(4) . . . . ? C14 C15 C20 C19 -178.6(2) . . . . ? C15 C20 C19 C18 -1.3(4) . . . . ? C15 C16 C17 C18 0.0(4) . . . . ? C20 C19 C18 C17 0.8(5) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.224 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.038 #=========# data_Compound_III _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H48 N4 O5' _chemical_formula_sum 'C44 H48 N4 O5' _chemical_formula_weight 712.86 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0564(17) _cell_length_b 7.4268(17) _cell_length_c 18.270(4) _cell_angle_alpha 90.823(5) _cell_angle_beta 91.860(5) _cell_angle_gamma 109.877(3) _cell_volume 899.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.5 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\p and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4916 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3277 _reflns_number_gt 2220 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 3' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1545P)^2^+0.3628P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3277 _refine_ls_number_parameters 249 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0769 _refine_ls_wR_factor_ref 0.2519 _refine_ls_wR_factor_gt 0.2175 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.025 _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 O1 O 0.5349(5) 0.2530(4) 0.52950(13) 0.0494(8) Uani 1 1 d . . . O2 O -0.0233(4) -0.7527(3) 0.77801(12) 0.0304(6) Uani 1 1 d . . . N1 N 0.5954(4) 0.4163(4) 0.64218(14) 0.0241(6) Uani 1 1 d . . . N2 N 0.4632(4) 0.1735(4) 0.71916(14) 0.0235(7) Uani 1 1 d . . . C21 C 0.8000(5) 0.9902(5) 1.09094(18) 0.0321(8) Uani 1 1 d . . . H21A H 0.7642 0.9195 1.1350 0.048 Uiso 1 1 calc R . . H21B H 0.7223 1.0734 1.0854 0.048 Uiso 1 1 calc R . . H21C H 0.9410 1.0651 1.0938 0.048 Uiso 1 1 calc R . . C16 C 0.7570(5) 0.8532(5) 1.02628(18) 0.0275(8) Uani 1 1 d . . . C15 C 0.6741(5) 0.8915(5) 0.96041(18) 0.0263(8) Uani 1 1 d . . . H15 H 0.6484 1.0058 0.9564 0.032 Uiso 1 1 calc R . . C14 C 0.6293(5) 0.7652(5) 0.90120(18) 0.0251(7) Uani 1 1 d . . . H14 H 0.5710 0.7937 0.8585 0.030 Uiso 1 1 calc R . . C13 C 0.6712(5) 0.5933(5) 0.90505(17) 0.0262(8) Uani 1 1 d . . . C18 C 0.7548(5) 0.5558(5) 0.97078(18) 0.0279(8) Uani 1 1 d . . . H18 H 0.7821 0.4422 0.9749 0.033 Uiso 1 1 calc R . . C17 C 0.7980(5) 0.6831(5) 1.02993(18) 0.0291(8) Uani 1 1 d . . . H17 H 0.8554 0.6547 1.0728 0.035 Uiso 1 1 calc R . . C12 C 0.6277(5) 0.4567(5) 0.84315(17) 0.0249(7) Uani 1 1 d . . . H12 H 0.6178 0.3314 0.8531 0.030 Uiso 1 1 calc R . . C11 C 0.6012(5) 0.4972(5) 0.77367(18) 0.0249(7) Uani 1 1 d . . . H11 H 0.6156 0.6231 0.7630 0.030 Uiso 1 1 calc R . . C1 C 0.5516(5) 0.3581(4) 0.71365(17) 0.0222(7) Uani 1 1 d . . . C3 C 0.5257(5) 0.2544(5) 0.59634(19) 0.0295(8) Uani 1 1 d . . . C2 C 0.4428(5) 0.0972(4) 0.64799(16) 0.0232(7) Uani 1 1 d . . . C20 C 0.6996(5) 0.6075(5) 0.6173(2) 0.0315(8) Uani 1 1 d . . . H20A H 0.7041 0.6047 0.5648 0.047 Uiso 1 1 calc R . . H20B H 0.8346 0.6532 0.6382 0.047 Uiso 1 1 calc R . . H20C H 0.6294 0.6913 0.6322 0.047 Uiso 1 1 calc R . . C4 C 0.3585(5) -0.0873(5) 0.62396(17) 0.0256(8) Uani 1 1 d . . . H4 H 0.3636 -0.1076 0.5738 0.031 Uiso 1 1 calc R . . C5 C 0.2619(5) -0.2572(4) 0.66473(17) 0.0217(7) Uani 1 1 d . . . C6 C 0.2311(5) -0.2538(4) 0.74078(16) 0.0227(7) Uani 1 1 d . . . H6 H 0.2761 -0.1381 0.7672 0.027 Uiso 1 1 calc R . . C7 C 0.1349(5) -0.4210(5) 0.77590(17) 0.0246(7) Uani 1 1 d . . . H7 H 0.1159 -0.4170 0.8259 0.030 Uiso 1 1 calc R . . C8 C 0.0652(5) -0.5972(4) 0.73740(17) 0.0234(7) Uani 1 1 d . . . C9 C 0.0919(5) -0.6031(4) 0.66221(17) 0.0246(7) Uani 1 1 d . . . H9 H 0.0453 -0.7191 0.6360 0.030 Uiso 1 1 calc R . . C10 C 0.1879(5) -0.4354(5) 0.62720(17) 0.0242(7) Uani 1 1 d . . . H10 H 0.2044 -0.4402 0.5770 0.029 Uiso 1 1 calc R . . C19 C -0.0862(5) -0.9351(5) 0.7412(2) 0.0305(8) Uani 1 1 d . . . H19A H -0.1831 -0.9387 0.7026 0.046 Uiso 1 1 calc R . . H19B H -0.1464 -1.0332 0.7754 0.046 Uiso 1 1 calc R . . H19C H 0.0285 -0.9562 0.7209 0.046 Uiso 1 1 calc R . . O3 O 1.0000 0.0000 0.5000 0.101(2) Uani 1 2 d SD . . C22 C 0.8616(8) 0.0179(7) 0.5444(3) 0.0600(13) Uani 1 1 d . . . H22A H 0.7309 -0.0670 0.5277 0.090 Uiso 1 1 calc R . . H22B H 0.8629 0.1476 0.5442 0.090 Uiso 1 1 calc R . . H22C H 0.8909 -0.0139 0.5932 0.090 Uiso 1 1 calc R . . H3S H 0.886(11) -0.078(12) 0.469(5) 0.20(5) 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 O1 0.097(2) 0.0307(15) 0.0240(14) 0.0042(11) 0.0235(14) 0.0242(15) O2 0.0329(14) 0.0225(13) 0.0318(13) 0.0006(10) 0.0033(10) 0.0038(10) N1 0.0250(15) 0.0206(14) 0.0279(15) 0.0036(11) 0.0067(11) 0.0087(11) N2 0.0238(15) 0.0271(15) 0.0205(14) -0.0023(11) 0.0007(11) 0.0098(12) C21 0.027(2) 0.041(2) 0.0265(18) -0.0086(15) -0.0020(14) 0.0093(16) C16 0.0219(18) 0.0307(18) 0.0264(17) -0.0042(14) 0.0016(14) 0.0046(14) C15 0.0223(17) 0.0242(17) 0.0314(18) -0.0013(14) 0.0036(14) 0.0065(13) C14 0.0214(18) 0.0283(18) 0.0234(16) -0.0007(13) 0.0003(13) 0.0056(14) C13 0.0214(18) 0.0263(18) 0.0271(18) -0.0015(14) 0.0019(14) 0.0033(13) C18 0.0271(19) 0.0240(17) 0.0313(18) 0.0029(14) 0.0022(14) 0.0067(14) C17 0.029(2) 0.0327(19) 0.0231(17) 0.0017(14) -0.0008(14) 0.0075(15) C12 0.0180(17) 0.0248(17) 0.0300(18) -0.0003(14) 0.0024(13) 0.0050(13) C11 0.0195(17) 0.0208(17) 0.0330(18) -0.0026(13) 0.0004(14) 0.0052(13) C1 0.0184(16) 0.0238(17) 0.0250(17) -0.0014(13) 0.0001(13) 0.0082(13) C3 0.038(2) 0.0245(18) 0.0305(19) -0.0001(14) 0.0098(15) 0.0155(15) C2 0.0280(18) 0.0227(17) 0.0204(16) 0.0007(13) 0.0039(13) 0.0103(14) C20 0.029(2) 0.0267(18) 0.039(2) 0.0082(15) 0.0099(16) 0.0088(15) C4 0.033(2) 0.0284(18) 0.0212(16) -0.0001(13) 0.0018(14) 0.0171(15) C5 0.0195(17) 0.0242(17) 0.0246(16) -0.0011(13) -0.0016(13) 0.0116(13) C6 0.0241(18) 0.0216(17) 0.0240(16) -0.0018(13) -0.0012(13) 0.0102(13) C7 0.0260(18) 0.0282(18) 0.0200(16) -0.0041(13) 0.0003(13) 0.0100(14) C8 0.0206(17) 0.0218(17) 0.0287(18) 0.0021(13) 0.0009(13) 0.0084(13) C9 0.0271(19) 0.0216(17) 0.0261(17) -0.0047(13) -0.0016(14) 0.0098(14) C10 0.0296(19) 0.0274(18) 0.0185(15) -0.0032(13) -0.0003(13) 0.0137(14) C19 0.031(2) 0.0202(17) 0.0371(19) 0.0005(14) -0.0001(15) 0.0048(14) O3 0.080(5) 0.121(6) 0.089(5) 0.002(4) -0.007(4) 0.019(4) C22 0.068(4) 0.056(3) 0.052(3) -0.005(2) 0.002(3) 0.016(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 C3 1.225(4) . ? O2 C8 1.356(4) . ? O2 C19 1.424(4) . ? N1 C3 1.389(4) . ? N1 C1 1.392(4) . ? N1 C20 1.447(4) . ? N2 C1 1.306(4) . ? N2 C2 1.394(4) . ? C21 C16 1.502(4) . ? C16 C17 1.391(5) . ? C16 C15 1.396(5) . ? C15 C14 1.377(4) . ? C14 C13 1.408(4) . ? C13 C18 1.394(4) . ? C13 C12 1.461(4) . ? C18 C17 1.382(5) . ? C12 C11 1.331(4) . ? C11 C1 1.445(4) . ? C3 C2 1.483(5) . ? C2 C4 1.355(5) . ? C4 C5 1.444(5) . ? C5 C10 1.405(4) . ? C5 C6 1.414(4) . ? C6 C7 1.376(4) . ? C7 C8 1.401(4) . ? C8 C9 1.395(4) . ? C9 C10 1.377(5) . ? O3 C22 1.329(5) 2_756 ? O3 C22 1.329(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 C8 O2 C19 117.1(3) . . ? C3 N1 C1 107.8(3) . . ? C3 N1 C20 124.1(3) . . ? C1 N1 C20 128.1(3) . . ? C1 N2 C2 105.8(3) . . ? C17 C16 C15 117.5(3) . . ? C17 C16 C21 121.1(3) . . ? C15 C16 C21 121.3(3) . . ? C14 C15 C16 122.0(3) . . ? C15 C14 C13 120.3(3) . . ? C18 C13 C14 117.6(3) . . ? C18 C13 C12 120.5(3) . . ? C14 C13 C12 121.9(3) . . ? C17 C18 C13 121.6(3) . . ? C18 C17 C16 121.0(3) . . ? C11 C12 C13 125.2(3) . . ? C12 C11 C1 124.2(3) . . ? N2 C1 N1 113.8(3) . . ? N2 C1 C11 125.7(3) . . ? N1 C1 C11 120.5(3) . . ? O1 C3 N1 125.5(3) . . ? O1 C3 C2 131.3(3) . . ? N1 C3 C2 103.1(3) . . ? C4 C2 N2 129.2(3) . . ? C4 C2 C3 121.4(3) . . ? N2 C2 C3 109.4(3) . . ? C2 C4 C5 129.5(3) . . ? C10 C5 C6 117.6(3) . . ? C10 C5 C4 119.0(3) . . ? C6 C5 C4 123.4(3) . . ? C7 C6 C5 120.3(3) . . ? C6 C7 C8 121.0(3) . . ? O2 C8 C9 124.7(3) . . ? O2 C8 C7 115.8(3) . . ? C9 C8 C7 119.5(3) . . ? C10 C9 C8 119.3(3) . . ? C9 C10 C5 122.3(3) . . ? C22 O3 C22 180.0(4) 2_756 . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.477 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.088 #=========# data_Compound_IV _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 N2 O3' _chemical_formula_sum 'C21 H18 N2 O3' _chemical_formula_weight 346.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 4.9084(17) _cell_length_b 14.926(5) _cell_length_c 12.013(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.761(7) _cell_angle_gamma 90.00 _cell_volume 867.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3183 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.16 _exptl_crystal_description Needle _exptl_crystal_colour Red _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.986 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6267 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2880 _reflns_number_gt 2428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.1171P)^2^+0.0134P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(1) _refine_ls_number_reflns 2880 _refine_ls_number_parameters 235 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1565 _refine_ls_wR_factor_gt 0.1449 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 O1 O -0.2856(6) 0.48483(15) 1.2285(2) 0.0793(8) Uani 1 1 d . . . O2 O 1.1209(7) 0.6247(3) 0.4137(3) 0.0977(10) Uani 1 1 d . . . O3 O -0.5015(7) 1.00573(16) 0.9233(3) 0.0833(8) Uani 1 1 d . . . C15 C 0.4546(6) 0.77108(17) 0.6344(2) 0.0436(6) Uani 1 1 d . . . N2 N -0.1972(6) 0.95673(15) 0.8090(2) 0.0567(6) Uani 1 1 d . . . C1 C -0.3996(10) 0.4675(3) 1.3269(3) 0.0856(13) Uani 1 1 d . . . H1A H -0.3525 0.4078 1.3529 0.128 Uiso 1 1 calc R . . H1B H -0.5970 0.4734 1.3099 0.128 Uiso 1 1 calc R . . H1C H -0.3266 0.5096 1.3848 0.128 Uiso 1 1 calc R . . C2 C -0.3289(7) 0.5661(2) 1.1788(2) 0.0580(8) Uani 1 1 d . . . C3 C -0.4945(8) 0.6314(3) 1.2121(3) 0.0649(9) Uani 1 1 d . . . H3 H -0.5902 0.6207 1.2713 0.078 Uiso 1 1 calc R . . C4 C -0.5183(7) 0.7129(2) 1.1576(3) 0.0636(8) Uani 1 1 d . . . H4 H -0.6341 0.7562 1.1801 0.076 Uiso 1 1 calc R . . C5 C -0.3750(6) 0.7331(2) 1.0699(2) 0.0527(7) Uani 1 1 d . . . C8 C -0.4013(7) 0.8206(2) 1.0202(2) 0.0557(7) Uani 1 1 d . . . H8 H -0.5249 0.8582 1.0483 0.067 Uiso 1 1 calc R . . C9 C -0.2767(7) 0.85783(19) 0.9395(2) 0.0513(7) Uani 1 1 d . . . N1 N -0.0878(5) 0.81941(15) 0.87926(19) 0.0486(6) Uani 1 1 d . . . C11 C -0.0504(6) 0.87850(18) 0.8042(2) 0.0487(7) Uani 1 1 d . . . C13 C 0.1278(6) 0.86617(19) 0.7199(2) 0.0492(7) Uani 1 1 d . . . H13 H 0.1396 0.9116 0.6680 0.059 Uiso 1 1 calc R . . C14 C 0.2735(6) 0.79202(18) 0.7152(2) 0.0458(6) Uani 1 1 d . . . H14 H 0.2586 0.7486 0.7693 0.055 Uiso 1 1 calc R . . C16 C 0.5011(7) 0.8292(2) 0.5495(2) 0.0528(7) Uani 1 1 d . . . H16 H 0.4120 0.8844 0.5414 0.063 Uiso 1 1 calc R . . C17 C 0.6803(7) 0.8054(2) 0.4764(2) 0.0579(8) Uani 1 1 d . . . H17 H 0.7122 0.8453 0.4206 0.070 Uiso 1 1 calc R . . C18 C 0.8116(6) 0.7233(2) 0.4855(2) 0.0516(7) Uani 1 1 d . . . C21 C 1.0013(8) 0.6979(3) 0.4095(3) 0.0666(9) Uani 1 1 d . . . H21 H 1.0339 0.7389 0.3550 0.080 Uiso 1 1 calc R . . C6 C -0.2084(8) 0.6652(2) 1.0366(3) 0.0630(8) Uani 1 1 d . . . H6 H -0.1100 0.6758 0.9782 0.076 Uiso 1 1 calc R . . C7 C -0.1891(8) 0.5831(2) 1.0895(3) 0.0701(10) Uani 1 1 d . . . H7 H -0.0811 0.5383 1.0653 0.084 Uiso 1 1 calc R . . C10 C -0.3491(7) 0.94791(19) 0.8951(3) 0.0611(8) Uani 1 1 d . . . C12 C -0.1995(10) 1.0363(2) 0.7392(4) 0.0770(10) Uani 1 1 d . . . H12A H -0.0789 1.0275 0.6851 0.115 Uiso 1 1 calc R . . H12B H -0.1370 1.0868 0.7862 0.115 Uiso 1 1 calc R . . H12C H -0.3840 1.0472 0.7004 0.115 Uiso 1 1 calc R . . C19 C 0.7593(7) 0.6642(2) 0.5692(2) 0.0538(7) Uani 1 1 d . . . H19 H 0.8420 0.6079 0.5753 0.065 Uiso 1 1 calc R . . C20 C 0.5861(6) 0.68847(18) 0.6428(2) 0.0502(7) Uani 1 1 d . . . H20 H 0.5565 0.6488 0.6992 0.060 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 O1 0.116(2) 0.0590(12) 0.0739(14) -0.0035(11) 0.0476(15) -0.0023(14) O2 0.085(2) 0.125(3) 0.0905(19) -0.0246(17) 0.0350(17) 0.0079(19) O3 0.092(2) 0.0568(13) 0.1112(19) -0.0130(13) 0.0465(16) 0.0118(13) C15 0.0393(16) 0.0514(14) 0.0417(12) -0.0017(10) 0.0112(11) -0.0090(12) N2 0.0583(18) 0.0470(12) 0.0674(14) -0.0066(11) 0.0181(12) -0.0016(11) C1 0.120(4) 0.068(2) 0.081(2) -0.0022(17) 0.053(2) -0.012(2) C2 0.066(2) 0.0569(16) 0.0549(14) -0.0106(12) 0.0199(14) -0.0098(14) C3 0.069(2) 0.077(2) 0.0575(15) -0.0100(14) 0.0372(16) -0.0073(16) C4 0.063(2) 0.0734(19) 0.0628(18) -0.0060(15) 0.0352(16) 0.0081(16) C5 0.0477(18) 0.069(2) 0.0446(13) -0.0112(12) 0.0177(12) -0.0024(14) C8 0.0559(19) 0.0631(17) 0.0524(15) -0.0173(13) 0.0212(14) 0.0041(14) C9 0.0512(19) 0.0571(15) 0.0471(14) -0.0116(12) 0.0124(13) 0.0006(13) N1 0.0465(14) 0.0555(13) 0.0465(11) -0.0064(10) 0.0153(10) -0.0002(11) C11 0.0464(17) 0.0484(14) 0.0523(14) -0.0082(11) 0.0111(12) -0.0044(12) C13 0.0488(18) 0.0511(15) 0.0499(13) -0.0013(11) 0.0140(13) -0.0066(12) C14 0.0438(18) 0.0528(14) 0.0430(12) 0.0005(10) 0.0138(12) -0.0071(12) C16 0.0529(19) 0.0535(15) 0.0531(14) 0.0007(12) 0.0119(14) -0.0021(13) C17 0.056(2) 0.072(2) 0.0487(14) 0.0063(13) 0.0158(14) -0.0161(15) C18 0.0402(17) 0.0674(18) 0.0483(14) -0.0085(12) 0.0104(12) -0.0082(13) C21 0.050(2) 0.097(3) 0.0559(16) -0.0137(17) 0.0165(14) -0.0136(19) C6 0.074(3) 0.0660(18) 0.0577(15) -0.0055(14) 0.0361(16) 0.0037(16) C7 0.085(3) 0.0660(19) 0.0695(19) -0.0081(15) 0.0419(19) 0.0099(18) C10 0.064(2) 0.0492(15) 0.0715(18) -0.0180(14) 0.0157(17) 0.0004(14) C12 0.090(3) 0.0481(15) 0.098(2) 0.0064(17) 0.030(2) 0.0008(16) C19 0.0469(19) 0.0603(16) 0.0568(16) -0.0047(12) 0.0158(14) -0.0031(13) C20 0.0510(19) 0.0519(15) 0.0506(14) 0.0035(11) 0.0172(13) -0.0024(13) _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 C2 1.353(4) . ? O1 C1 1.415(4) . ? O2 C21 1.236(5) . ? O3 C10 1.227(4) . ? C15 C16 1.387(4) . ? C15 C20 1.387(4) . ? C15 C14 1.457(4) . ? N2 C11 1.378(4) . ? N2 C10 1.381(4) . ? N2 C12 1.453(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.372(5) . ? C2 C7 1.390(5) . ? C3 C4 1.377(5) . ? C3 H3 0.9300 . ? C4 C5 1.395(4) . ? C4 H4 0.9300 . ? C5 C6 1.402(5) . ? C5 C8 1.433(5) . ? C8 C9 1.350(5) . ? C8 H8 0.9300 . ? C9 N1 1.393(4) . ? C9 C10 1.468(4) . ? N1 C11 1.297(4) . ? C11 C13 1.458(4) . ? C13 C14 1.324(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C16 C17 1.390(5) . ? C16 H16 0.9300 . ? C17 C18 1.381(5) . ? C17 H17 0.9300 . ? C18 C19 1.394(4) . ? C18 C21 1.460(5) . ? C21 H21 0.9300 . ? C6 C7 1.377(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C19 C20 1.375(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 118.5(3) . . ? C16 C15 C20 118.4(3) . . ? C16 C15 C14 123.4(3) . . ? C20 C15 C14 118.1(2) . . ? C11 N2 C10 107.7(2) . . ? C11 N2 C12 128.4(3) . . ? C10 N2 C12 123.9(3) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 124.4(3) . . ? O1 C2 C7 116.3(3) . . ? C3 C2 C7 119.3(3) . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 122.5(3) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 116.9(3) . . ? C4 C5 C8 119.3(3) . . ? C6 C5 C8 123.8(3) . . ? C9 C8 C5 130.8(3) . . ? C9 C8 H8 114.6 . . ? C5 C8 H8 114.6 . . ? C8 C9 N1 128.8(3) . . ? C8 C9 C10 121.7(3) . . ? N1 C9 C10 109.3(3) . . ? C11 N1 C9 105.5(2) . . ? N1 C11 N2 114.2(3) . . ? N1 C11 C13 124.7(3) . . ? N2 C11 C13 121.0(2) . . ? C14 C13 C11 121.8(2) . . ? C14 C13 H13 119.1 . . ? C11 C13 H13 119.1 . . ? C13 C14 C15 127.1(2) . . ? C13 C14 H14 116.5 . . ? C15 C14 H14 116.5 . . ? C15 C16 C17 120.4(3) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 120.9(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 118.6(3) . . ? C17 C18 C21 121.3(3) . . ? C19 C18 C21 120.1(3) . . ? O2 C21 C18 123.6(4) . . ? O2 C21 H21 118.2 . . ? C18 C21 H21 118.2 . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 121.0(3) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? O3 C10 N2 124.9(3) . . ? O3 C10 C9 131.8(3) . . ? N2 C10 C9 103.4(2) . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C15 121.3(3) . . ? C19 C20 H20 119.4 . . ? C15 C20 H20 119.4 . . ? 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 C1 O1 C2 C3 -5.2(5) . . . . ? C1 O1 C2 C7 173.5(3) . . . . ? O1 C2 C3 C4 178.2(3) . . . . ? C7 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C5 -1.3(5) . . . . ? C3 C4 C5 C6 1.7(5) . . . . ? C3 C4 C5 C8 -177.5(3) . . . . ? C4 C5 C8 C9 176.4(3) . . . . ? C6 C5 C8 C9 -2.6(5) . . . . ? C5 C8 C9 N1 1.5(5) . . . . ? C5 C8 C9 C10 175.7(3) . . . . ? C8 C9 N1 C11 173.8(3) . . . . ? C10 C9 N1 C11 -1.0(3) . . . . ? C9 N1 C11 N2 1.1(3) . . . . ? C9 N1 C11 C13 -178.5(3) . . . . ? C10 N2 C11 N1 -0.7(3) . . . . ? C12 N2 C11 N1 178.9(3) . . . . ? C10 N2 C11 C13 178.9(3) . . . . ? C12 N2 C11 C13 -1.4(5) . . . . ? N1 C11 C13 C14 -1.4(4) . . . . ? N2 C11 C13 C14 179.0(3) . . . . ? C11 C13 C14 C15 179.0(3) . . . . ? C16 C15 C14 C13 0.7(4) . . . . ? C20 C15 C14 C13 -178.9(3) . . . . ? C20 C15 C16 C17 -1.4(4) . . . . ? C14 C15 C16 C17 179.0(3) . . . . ? C15 C16 C17 C18 1.1(4) . . . . ? C16 C17 C18 C19 0.5(4) . . . . ? C16 C17 C18 C21 -179.7(3) . . . . ? C17 C18 C21 O2 -179.2(4) . . . . ? C19 C18 C21 O2 0.7(5) . . . . ? C4 C5 C6 C7 -0.3(5) . . . . ? C8 C5 C6 C7 178.8(3) . . . . ? C5 C6 C7 C2 -1.5(6) . . . . ? O1 C2 C7 C6 -176.9(3) . . . . ? C3 C2 C7 C6 1.9(6) . . . . ? C11 N2 C10 O3 179.3(3) . . . . ? C12 N2 C10 O3 -0.4(5) . . . . ? C11 N2 C10 C9 0.0(3) . . . . ? C12 N2 C10 C9 -179.6(3) . . . . ? C8 C9 C10 O3 6.2(5) . . . . ? N1 C9 C10 O3 -178.6(4) . . . . ? C8 C9 C10 N2 -174.6(3) . . . . ? N1 C9 C10 N2 0.6(3) . . . . ? C17 C18 C19 C20 -1.7(4) . . . . ? C21 C18 C19 C20 178.4(3) . . . . ? C18 C19 C20 C15 1.4(4) . . . . ? C16 C15 C20 C19 0.1(4) . . . . ? C14 C15 C20 C19 179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.539 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.051