data_4100 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N O3' _chemical_formula_weight 332.36 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2627(13) _cell_length_b 10.0415(16) _cell_length_c 10.3726(17) _cell_angle_alpha 90.401(3) _cell_angle_beta 102.338(3) _cell_angle_gamma 96.760(4) _cell_volume 834.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 724 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.40 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 350 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.9570 _exptl_absorpt_correction_T_max 0.9773 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 5840 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3770 _reflns_number_gt 2843 _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^)+(0.0695P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3770 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.05734(14) 0.08822(10) 0.67910(11) 0.0446(3) Uani 1 1 d . . . H1A H 0.131(2) 0.042(2) 0.7223(18) 0.065(6) Uiso 1 1 d . . . O2 O 0.28112(15) 0.92306(10) 0.80676(11) 0.0480(3) Uani 1 1 d . . . H2A H 0.340(3) 0.907(2) 0.748(2) 0.080(6) Uiso 1 1 d . . . O3 O 0.42110(13) 0.63166(11) 0.51464(10) 0.0434(3) Uani 1 1 d . . . H3A H 0.469(2) 0.624(2) 0.453(2) 0.080(7) Uiso 1 1 d . . . N1 N 0.43565(15) 0.95878(12) 0.60778(11) 0.0408(3) Uani 1 1 d . . . C1 C 0.31103(15) 0.64184(12) 0.74875(12) 0.0273(3) Uani 1 1 d . . . H1 H 0.2477 0.6901 0.6756 0.033 Uiso 1 1 calc R . . C2 C 0.25103(15) 0.49218(12) 0.72208(11) 0.0273(3) Uani 1 1 d . . . C3 C 0.35293(16) 0.39442(13) 0.76720(13) 0.0324(3) Uani 1 1 d . . . H3 H 0.4654 0.4203 0.8080 0.039 Uiso 1 1 calc R . . C4 C 0.29197(17) 0.25902(13) 0.75317(13) 0.0345(3) Uani 1 1 d . . . H4 H 0.3628 0.1943 0.7849 0.041 Uiso 1 1 calc R . . C5 C 0.12720(16) 0.21946(13) 0.69261(13) 0.0320(3) Uani 1 1 d . . . C6 C 0.02517(16) 0.31578(13) 0.64289(13) 0.0324(3) Uani 1 1 d . . . H6 H -0.0859 0.2896 0.5986 0.039 Uiso 1 1 calc R . . C7 C 0.08701(15) 0.45014(13) 0.65857(12) 0.0297(3) Uani 1 1 d . . . H7 H 0.0165 0.5146 0.6255 0.036 Uiso 1 1 calc R . . C8 C 0.27065(15) 0.69211(12) 0.87627(12) 0.0279(3) Uani 1 1 d . . . C9 C 0.23848(17) 0.60562(14) 0.97432(13) 0.0351(3) Uani 1 1 d . . . H9 H 0.2426 0.5133 0.9620 0.042 Uiso 1 1 calc R . . C10 C 0.20067(18) 0.65070(15) 1.08932(13) 0.0405(3) Uani 1 1 d . . . H10 H 0.1788 0.5896 1.1535 0.049 Uiso 1 1 calc R . . C11 C 0.19515(18) 0.78533(15) 1.10936(14) 0.0429(4) Uani 1 1 d . . . H11 H 0.1704 0.8167 1.1877 0.051 Uiso 1 1 calc R . . C12 C 0.22603(18) 0.87422(15) 1.01428(14) 0.0421(4) Uani 1 1 d . . . H12 H 0.2225 0.9664 1.0279 0.051 Uiso 1 1 calc R . . C13 C 0.26231(16) 0.82806(13) 0.89835(13) 0.0331(3) Uani 1 1 d . . . C14 C 0.49508(15) 0.67319(12) 0.74545(12) 0.0283(3) Uani 1 1 d . . . C15 C 0.54510(16) 0.66150(13) 0.62601(13) 0.0329(3) Uani 1 1 d . . . C16 C 0.71157(19) 0.68230(14) 0.61973(16) 0.0430(4) Uani 1 1 d . . . H16 H 0.7431 0.6721 0.5387 0.052 Uiso 1 1 calc R . . C17 C 0.83097(18) 0.71803(15) 0.73296(17) 0.0476(4) Uani 1 1 d . . . H17 H 0.9442 0.7329 0.7288 0.057 Uiso 1 1 calc R . . C18 C 0.78597(18) 0.73206(15) 0.85207(16) 0.0454(4) Uani 1 1 d . . . H18 H 0.8677 0.7570 0.9291 0.055 Uiso 1 1 calc R . . C19 C 0.61854(17) 0.70900(14) 0.85740(14) 0.0363(3) Uani 1 1 d . . . H19 H 0.5882 0.7179 0.9391 0.044 Uiso 1 1 calc R . . C20 C 0.33706(18) 0.97850(14) 0.49245(15) 0.0409(3) Uani 1 1 d . . . H20 H 0.2207 0.9643 0.4837 0.049 Uiso 1 1 calc R . . C21 C 0.59879(19) 0.98070(14) 0.61461(14) 0.0407(3) Uani 1 1 d . . . H21 H 0.6725 0.9680 0.6949 0.049 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 0.0492(6) 0.0273(5) 0.0560(7) 0.0021(5) 0.0105(5) 0.0007(5) O2 0.0763(7) 0.0275(5) 0.0542(7) 0.0126(5) 0.0400(6) 0.0154(5) O3 0.0527(6) 0.0482(7) 0.0318(5) -0.0041(5) 0.0152(5) 0.0056(5) N1 0.0553(8) 0.0324(6) 0.0402(7) 0.0071(5) 0.0206(6) 0.0092(5) C1 0.0337(7) 0.0245(6) 0.0252(6) 0.0045(5) 0.0069(5) 0.0084(5) C2 0.0340(7) 0.0256(6) 0.0239(6) 0.0023(5) 0.0090(5) 0.0056(5) C3 0.0337(7) 0.0288(7) 0.0337(7) 0.0024(5) 0.0040(5) 0.0057(5) C4 0.0415(7) 0.0273(7) 0.0363(7) 0.0052(5) 0.0082(6) 0.0110(5) C5 0.0407(7) 0.0260(7) 0.0309(7) -0.0002(5) 0.0122(5) 0.0018(5) C6 0.0317(7) 0.0359(7) 0.0303(7) 0.0010(5) 0.0085(5) 0.0035(5) C7 0.0349(7) 0.0300(7) 0.0272(6) 0.0040(5) 0.0093(5) 0.0105(5) C8 0.0302(6) 0.0270(6) 0.0274(6) 0.0030(5) 0.0078(5) 0.0048(5) C9 0.0441(8) 0.0304(7) 0.0329(7) 0.0067(6) 0.0107(6) 0.0088(6) C10 0.0488(8) 0.0438(8) 0.0310(7) 0.0081(6) 0.0136(6) 0.0046(6) C11 0.0504(9) 0.0474(9) 0.0343(7) -0.0053(6) 0.0197(6) 0.0003(7) C12 0.0544(9) 0.0323(7) 0.0440(8) -0.0054(6) 0.0222(7) 0.0026(6) C13 0.0387(7) 0.0279(7) 0.0358(7) 0.0045(5) 0.0153(6) 0.0040(5) C14 0.0345(7) 0.0193(6) 0.0330(7) 0.0034(5) 0.0094(5) 0.0070(5) C15 0.0414(7) 0.0237(6) 0.0359(7) 0.0010(5) 0.0123(6) 0.0056(5) C16 0.0480(8) 0.0347(8) 0.0540(9) -0.0006(7) 0.0265(7) 0.0080(6) C17 0.0358(8) 0.0402(9) 0.0710(11) 0.0015(8) 0.0189(7) 0.0083(6) C18 0.0378(8) 0.0398(8) 0.0550(9) 0.0022(7) 0.0009(7) 0.0061(6) C19 0.0416(8) 0.0322(7) 0.0352(7) 0.0046(6) 0.0069(6) 0.0072(6) C20 0.0403(8) 0.0327(7) 0.0509(9) 0.0038(6) 0.0125(7) 0.0044(6) C21 0.0535(9) 0.0320(7) 0.0349(7) 0.0034(6) 0.0042(6) 0.0083(6) _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 C5 1.3688(16) . ? O2 C13 1.3702(16) . ? O3 C15 1.3752(17) . ? N1 C20 1.3261(19) . ? N1 C21 1.3266(19) . ? C1 C14 1.5240(17) . ? C1 C8 1.5280(16) . ? C1 C2 1.5299(17) . ? C2 C3 1.3871(17) . ? C2 C7 1.3888(18) . ? C3 C4 1.3886(18) . ? C4 C5 1.3819(19) . ? C5 C6 1.3875(19) . ? C6 C7 1.3809(18) . ? C8 C9 1.3903(18) . ? C8 C13 1.3947(18) . ? C9 C10 1.3822(18) . ? C10 C11 1.374(2) . ? C11 C12 1.379(2) . ? C12 C13 1.3891(18) . ? C14 C19 1.3856(18) . ? C14 C15 1.3955(18) . ? C15 C16 1.382(2) . ? C16 C17 1.377(2) . ? C17 C18 1.375(2) . ? C18 C19 1.389(2) . ? C20 C21 1.374(2) 2_676 ? C21 C20 1.374(2) 2_676 ? 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 C20 N1 C21 116.72(12) . . ? C14 C1 C8 112.92(10) . . ? C14 C1 C2 111.21(9) . . ? C8 C1 C2 111.41(10) . . ? C3 C2 C7 117.81(12) . . ? C3 C2 C1 121.93(11) . . ? C7 C2 C1 120.13(10) . . ? C2 C3 C4 121.25(12) . . ? C5 C4 C3 120.00(12) . . ? O1 C5 C4 123.17(12) . . ? O1 C5 C6 117.38(12) . . ? C4 C5 C6 119.45(12) . . ? C7 C6 C5 119.90(12) . . ? C6 C7 C2 121.53(12) . . ? C9 C8 C13 116.96(12) . . ? C9 C8 C1 122.11(11) . . ? C13 C8 C1 120.92(11) . . ? C10 C9 C8 122.23(13) . . ? C11 C10 C9 119.67(13) . . ? C10 C11 C12 119.80(13) . . ? C11 C12 C13 120.23(13) . . ? O2 C13 C12 115.76(12) . . ? O2 C13 C8 123.07(12) . . ? C12 C13 C8 121.11(12) . . ? C19 C14 C15 117.44(12) . . ? C19 C14 C1 123.00(11) . . ? C15 C14 C1 119.52(11) . . ? O3 C15 C16 121.60(13) . . ? O3 C15 C14 116.98(11) . . ? C16 C15 C14 121.40(13) . . ? C17 C16 C15 119.59(14) . . ? C18 C17 C16 120.55(13) . . ? C17 C18 C19 119.30(14) . . ? C14 C19 C18 121.70(14) . . ? N1 C20 C21 121.49(14) . 2_676 ? N1 C21 C20 121.80(13) . 2_676 ? 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 O2 H2A N1 0.89(2) 1.85(2) 2.6548(16) 151(2) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.284 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.042