data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 N O2' _chemical_formula_weight 355.42 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' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5467(17) _cell_length_b 10.490(2) _cell_length_c 21.228(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.57(3) _cell_angle_gamma 90.00 _cell_volume 1864.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5493 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9740 _exptl_absorpt_correction_T_max 0.9834 _exptl_absorpt_process_details abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5493 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3272 _reflns_number_gt 2572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0726P)^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 0.0085(6) _refine_ls_number_reflns 3272 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _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 0.16964(15) 0.91413(13) 0.17686(6) 0.0434(4) Uani 1 1 d . . . O2 O 0.04978(16) 0.64884(13) 0.15790(6) 0.0436(4) Uani 1 1 d . . . N1 N 0.16224(17) 0.86344(14) 0.28183(7) 0.0321(4) Uani 1 1 d . . . C1 C 0.1207(2) 0.84959(17) 0.21645(8) 0.0325(4) Uani 1 1 d . . . C4 C 0.0965(2) 0.76026(17) 0.31245(8) 0.0320(4) Uani 1 1 d . . . C7 C -0.1624(2) 0.78457(17) 0.17162(8) 0.0336(4) Uani 1 1 d . . . C19 C 0.4348(2) 0.87963(19) 0.34965(9) 0.0373(5) Uani 1 1 d . . . C18 C 0.1051(2) 0.8525(2) 0.42262(9) 0.0414(5) Uani 1 1 d . . . H18A H 0.0877 0.9338 0.4052 0.050 Uiso 1 1 calc R . . C2 C 0.0034(2) 0.73551(18) 0.20254(9) 0.0339(4) Uani 1 1 d . . . C5 C 0.2903(2) 0.94863(18) 0.31256(9) 0.0380(5) Uani 1 1 d . . . H5A H 0.2493 1.0050 0.3416 0.046 Uiso 1 1 calc R . . H5B H 0.3230 1.0009 0.2798 0.046 Uiso 1 1 calc R . . C3 C 0.0105(2) 0.68405(18) 0.26892(9) 0.0371(5) Uani 1 1 d . . . H3A H -0.0385 0.6092 0.2783 0.045 Uiso 1 1 calc R . . C13 C 0.1190(2) 0.74966(18) 0.38302(8) 0.0334(5) Uani 1 1 d . . . C12 C -0.2173(2) 0.7803(2) 0.10594(10) 0.0460(5) Uani 1 1 d . . . H12A H -0.1530 0.7460 0.0797 0.055 Uiso 1 1 calc R . . C8 C -0.2603(3) 0.8375(2) 0.20882(10) 0.0524(6) Uani 1 1 d . . . H8A H -0.2259 0.8406 0.2532 0.063 Uiso 1 1 calc R . . C14 C 0.1459(3) 0.6294(2) 0.41043(9) 0.0471(5) Uani 1 1 d . . . H14A H 0.1566 0.5595 0.3847 0.056 Uiso 1 1 calc R . . C20 C 0.4921(2) 0.7691(2) 0.32699(11) 0.0504(6) Uani 1 1 d . . . H20A H 0.4385 0.7341 0.2884 0.061 Uiso 1 1 calc R . . C17 C 0.1170(3) 0.8346(2) 0.48779(10) 0.0492(6) Uani 1 1 d . . . H17A H 0.1074 0.9041 0.5140 0.059 Uiso 1 1 calc R . . C24 C 0.5158(2) 0.9288(2) 0.40766(10) 0.0491(6) Uani 1 1 d . . . H24A H 0.4790 1.0027 0.4241 0.059 Uiso 1 1 calc R . . C11 C -0.3671(3) 0.8266(2) 0.07879(10) 0.0567(6) Uani 1 1 d . . . H11A H -0.4033 0.8224 0.0345 0.068 Uiso 1 1 calc R . . C10 C -0.4623(3) 0.8786(2) 0.11677(12) 0.0584(6) Uani 1 1 d . . . H10A H -0.5635 0.9087 0.0984 0.070 Uiso 1 1 calc R . . C16 C 0.1429(3) 0.7150(2) 0.51439(10) 0.0531(6) Uani 1 1 d . . . H16A H 0.1508 0.7035 0.5584 0.064 Uiso 1 1 calc R . . C9 C -0.4082(3) 0.8860(3) 0.18154(11) 0.0606(7) Uani 1 1 d . . . H9A H -0.4711 0.9238 0.2074 0.073 Uiso 1 1 calc R . . C15 C 0.1568(3) 0.6132(2) 0.47579(10) 0.0564(6) Uani 1 1 d . . . H15A H 0.1738 0.5322 0.4936 0.068 Uiso 1 1 calc R . . C21 C 0.6278(3) 0.7095(3) 0.36067(12) 0.0602(7) Uani 1 1 d . . . H21A H 0.6653 0.6357 0.3445 0.072 Uiso 1 1 calc R . . C6 C 0.2095(3) 0.6041(2) 0.17549(10) 0.0574(6) Uani 1 1 d . . . H6A H 0.2314 0.5468 0.1431 0.086 Uiso 1 1 calc R . . H6B H 0.2233 0.5602 0.2159 0.086 Uiso 1 1 calc R . . H6C H 0.2816 0.6751 0.1794 0.086 Uiso 1 1 calc R . . C23 C 0.6511(3) 0.8685(3) 0.44121(11) 0.0618(7) Uani 1 1 d . . . H23A H 0.7050 0.9022 0.4801 0.074 Uiso 1 1 calc R . . C22 C 0.7063(3) 0.7594(3) 0.41757(12) 0.0609(7) Uani 1 1 d . . . H22A H 0.7974 0.7194 0.4404 0.073 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 0.0478(8) 0.0466(9) 0.0380(8) 0.0085(7) 0.0143(6) -0.0030(6) O2 0.0512(8) 0.0428(9) 0.0354(7) -0.0080(6) 0.0055(6) 0.0090(6) N1 0.0337(8) 0.0322(9) 0.0291(8) 0.0009(7) 0.0035(6) -0.0024(6) C1 0.0321(10) 0.0321(11) 0.0338(10) 0.0012(9) 0.0078(8) 0.0070(7) C4 0.0342(10) 0.0308(10) 0.0308(10) 0.0016(8) 0.0061(7) 0.0023(7) C7 0.0368(10) 0.0319(11) 0.0320(10) -0.0007(8) 0.0065(8) -0.0056(8) C19 0.0345(10) 0.0425(12) 0.0346(10) 0.0032(9) 0.0068(8) -0.0075(8) C18 0.0445(11) 0.0402(12) 0.0394(11) -0.0023(10) 0.0078(8) -0.0022(9) C2 0.0415(11) 0.0314(11) 0.0283(10) -0.0046(8) 0.0061(7) -0.0010(8) C5 0.0390(10) 0.0348(11) 0.0392(11) -0.0015(9) 0.0058(8) -0.0047(8) C3 0.0475(11) 0.0305(11) 0.0324(10) 0.0013(9) 0.0056(8) -0.0039(8) C13 0.0312(10) 0.0380(12) 0.0302(10) -0.0003(9) 0.0038(7) -0.0014(8) C12 0.0472(12) 0.0545(14) 0.0352(11) -0.0068(10) 0.0059(9) 0.0015(10) C8 0.0524(13) 0.0690(16) 0.0357(11) -0.0045(11) 0.0089(9) 0.0069(11) C14 0.0626(14) 0.0417(13) 0.0357(11) 0.0026(10) 0.0070(9) 0.0063(10) C20 0.0430(12) 0.0588(15) 0.0473(13) -0.0048(11) 0.0036(9) 0.0038(10) C17 0.0531(13) 0.0586(15) 0.0355(11) -0.0120(11) 0.0081(9) -0.0022(10) C24 0.0478(12) 0.0534(14) 0.0436(12) -0.0005(11) 0.0032(9) -0.0124(10) C11 0.0548(14) 0.0685(17) 0.0398(12) -0.0082(12) -0.0072(10) 0.0047(11) C10 0.0386(12) 0.0666(16) 0.0643(15) -0.0045(13) -0.0029(10) 0.0025(11) C16 0.0515(13) 0.0781(18) 0.0286(11) 0.0040(12) 0.0057(9) 0.0045(11) C9 0.0479(13) 0.0802(18) 0.0552(14) -0.0053(13) 0.0143(11) 0.0139(12) C15 0.0719(16) 0.0564(15) 0.0399(12) 0.0141(12) 0.0085(10) 0.0104(11) C21 0.0458(13) 0.0648(16) 0.0713(16) 0.0072(13) 0.0145(12) 0.0100(11) C6 0.0625(15) 0.0577(16) 0.0505(13) -0.0069(12) 0.0072(11) 0.0223(11) C23 0.0529(14) 0.079(2) 0.0463(13) 0.0110(13) -0.0071(10) -0.0162(13) C22 0.0362(12) 0.0779(19) 0.0644(16) 0.0264(14) 0.0004(11) -0.0048(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.217(2) . ? O2 C6 1.420(2) . ? O2 C2 1.426(2) . ? N1 C1 1.370(2) . ? N1 C4 1.434(2) . ? N1 C5 1.462(2) . ? C1 C2 1.551(3) . ? C4 C3 1.327(2) . ? C4 C13 1.476(3) . ? C7 C8 1.378(3) . ? C7 C12 1.380(3) . ? C7 C2 1.527(3) . ? C19 C20 1.382(3) . ? C19 C24 1.386(3) . ? C19 C5 1.509(3) . ? C18 C17 1.379(3) . ? C18 C13 1.387(3) . ? C18 H18A 0.9300 . ? C2 C3 1.499(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C3 H3A 0.9300 . ? C13 C14 1.389(3) . ? C12 C11 1.382(3) . ? C12 H12A 0.9300 . ? C8 C9 1.378(3) . ? C8 H8A 0.9300 . ? C14 C15 1.382(3) . ? C14 H14A 0.9300 . ? C20 C21 1.383(3) . ? C20 H20A 0.9300 . ? C17 C16 1.376(3) . ? C17 H17A 0.9300 . ? C24 C23 1.384(3) . ? C24 H24A 0.9300 . ? C11 C10 1.368(3) . ? C11 H11A 0.9300 . ? C10 C9 1.362(3) . ? C10 H10A 0.9300 . ? C16 C15 1.365(3) . ? C16 H16A 0.9300 . ? C9 H9A 0.9300 . ? C15 H15A 0.9300 . ? C21 C22 1.363(3) . ? C21 H21A 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C23 C22 1.371(4) . ? C23 H23A 0.9300 . ? C22 H22A 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 C6 O2 C2 114.60(14) . . ? C1 N1 C4 109.51(14) . . ? C1 N1 C5 122.39(15) . . ? C4 N1 C5 125.85(14) . . ? O1 C1 N1 125.87(17) . . ? O1 C1 C2 126.61(16) . . ? N1 C1 C2 107.50(15) . . ? C3 C4 N1 110.59(16) . . ? C3 C4 C13 127.06(17) . . ? N1 C4 C13 122.27(15) . . ? C8 C7 C12 118.01(18) . . ? C8 C7 C2 120.51(16) . . ? C12 C7 C2 121.46(17) . . ? C20 C19 C24 118.24(19) . . ? C20 C19 C5 122.05(17) . . ? C24 C19 C5 119.70(19) . . ? C17 C18 C13 120.29(19) . . ? C17 C18 H18A 119.9 . . ? C13 C18 H18A 119.9 . . ? O2 C2 C3 115.54(15) . . ? O2 C2 C7 106.68(13) . . ? C3 C2 C7 112.61(16) . . ? O2 C2 C1 111.30(15) . . ? C3 C2 C1 101.32(14) . . ? C7 C2 C1 109.31(14) . . ? N1 C5 C19 113.62(15) . . ? N1 C5 H5A 108.8 . . ? C19 C5 H5A 108.8 . . ? N1 C5 H5B 108.8 . . ? C19 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C4 C3 C2 110.49(17) . . ? C4 C3 H3A 124.8 . . ? C2 C3 H3A 124.8 . . ? C18 C13 C14 118.63(18) . . ? C18 C13 C4 123.17(17) . . ? C14 C13 C4 118.08(17) . . ? C7 C12 C11 120.6(2) . . ? C7 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C7 C8 C9 121.30(19) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C19 C20 C21 121.2(2) . . ? C19 C20 H20A 119.4 . . ? C21 C20 H20A 119.4 . . ? C16 C17 C18 120.6(2) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C23 C24 C19 120.3(2) . . ? C23 C24 H24A 119.9 . . ? C19 C24 H24A 119.9 . . ? C10 C11 C12 120.3(2) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C9 C10 C11 119.8(2) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C15 C16 C17 119.5(2) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C22 C21 C20 119.9(2) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? O2 C6 H6A 109.5 . . ? O2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.240 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.082