data_mo_dm11212_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H15 N O2' _chemical_formula_weight 349.37 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 P2(1)/n 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 14.1386(19) _cell_length_b 6.9808(10) _cell_length_c 17.394(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.471(2) _cell_angle_gamma 90.00 _cell_volume 1682.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 7348 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 30.75 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9699 _exptl_absorpt_correction_T_max 0.9809 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11378 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3624 _reflns_number_gt 3243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0849P)^2^+2.5149P] 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 3624 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1794 _refine_ls_wR_factor_gt 0.1754 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.89825(13) 0.7765(3) -0.05055(10) 0.0207(4) Uani 1 1 d . . . O1 O 1.19491(11) 0.7196(2) -0.04661(9) 0.0261(4) Uani 1 1 d . . . O2 O 1.09174(10) 0.6953(2) 0.15820(8) 0.0235(3) Uani 1 1 d . . . C1 C 0.99164(15) 0.7596(3) -0.04963(12) 0.0204(4) Uani 1 1 d . . . H1 H 1.0122 0.7701 -0.0983 0.024 Uiso 1 1 calc R . . C2 C 1.06242(15) 0.7275(3) 0.01768(12) 0.0186(4) Uani 1 1 d . . . C3 C 1.16511(15) 0.7059(3) 0.01466(12) 0.0195(4) Uani 1 1 d . . . C4 C 1.22767(15) 0.6685(3) 0.09170(12) 0.0201(4) Uani 1 1 d . . . C5 C 1.32739(16) 0.6368(3) 0.09977(13) 0.0262(5) Uani 1 1 d . . . H5 H 1.3555 0.6352 0.0545 0.031 Uiso 1 1 calc R . . C6 C 1.38443(16) 0.6081(4) 0.17260(14) 0.0296(5) Uani 1 1 d . . . H6 H 1.4515 0.5839 0.1774 0.036 Uiso 1 1 calc R . . C7 C 1.34400(16) 0.6145(4) 0.23959(14) 0.0292(5) Uani 1 1 d . . . H7 H 1.3841 0.5971 0.2898 0.035 Uiso 1 1 calc R . . C8 C 1.24637(16) 0.6456(4) 0.23363(13) 0.0273(5) Uani 1 1 d . . . H8 H 1.2189 0.6511 0.2792 0.033 Uiso 1 1 calc R . . C9 C 1.18907(15) 0.6689(3) 0.15926(12) 0.0210(4) Uani 1 1 d . . . C10 C 1.03025(15) 0.7194(3) 0.08829(12) 0.0186(4) Uani 1 1 d . . . C11 C 0.93227(15) 0.7417(3) 0.09097(11) 0.0182(4) Uani 1 1 d . . . C12 C 0.86754(14) 0.7643(3) 0.01878(12) 0.0180(4) Uani 1 1 d . . . C13 C 0.76090(14) 0.7747(3) 0.01040(12) 0.0192(4) Uani 1 1 d . . . C14 C 0.70767(16) 0.8751(3) -0.05334(12) 0.0232(4) Uani 1 1 d . . . H14 H 0.7407 0.9398 -0.0882 0.028 Uiso 1 1 calc R . . C15 C 0.60781(16) 0.8821(3) -0.06671(14) 0.0282(5) Uani 1 1 d . . . H15 H 0.5732 0.9522 -0.1101 0.034 Uiso 1 1 calc R . . C16 C 0.55819(16) 0.7867(3) -0.01682(14) 0.0282(5) Uani 1 1 d . . . H16 H 0.4897 0.7911 -0.0258 0.034 Uiso 1 1 calc R . . C17 C 0.61010(16) 0.6846(3) 0.04653(13) 0.0255(5) Uani 1 1 d . . . H17 H 0.5767 0.6184 0.0807 0.031 Uiso 1 1 calc R . . C18 C 0.71039(15) 0.6786(3) 0.06022(12) 0.0225(4) Uani 1 1 d . . . H18 H 0.7449 0.6087 0.1038 0.027 Uiso 1 1 calc R . . C19 C 0.90392(14) 0.7495(3) 0.16911(12) 0.0202(4) Uani 1 1 d . . . C20 C 0.86545(15) 0.9184(3) 0.19288(12) 0.0241(5) Uani 1 1 d . . . H20 H 0.8572 1.0271 0.1593 0.029 Uiso 1 1 calc R . . C21 C 0.83913(16) 0.9276(4) 0.26578(13) 0.0303(5) Uani 1 1 d . . . H21 H 0.8139 1.0434 0.2822 0.036 Uiso 1 1 calc R . . C22 C 0.84944(16) 0.7689(4) 0.31458(13) 0.0320(6) Uani 1 1 d . . . H22 H 0.8304 0.7753 0.3639 0.038 Uiso 1 1 calc R . . C23 C 0.88763(16) 0.6006(4) 0.29126(13) 0.0303(5) Uani 1 1 d . . . H23 H 0.8948 0.4918 0.3247 0.036 Uiso 1 1 calc R . . C24 C 0.91561(15) 0.5905(3) 0.21889(12) 0.0251(5) Uani 1 1 d . . . H24 H 0.9426 0.4756 0.2034 0.030 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 0.0222(9) 0.0236(9) 0.0167(8) 0.0008(7) 0.0051(6) -0.0009(7) O1 0.0245(8) 0.0342(9) 0.0221(8) 0.0013(6) 0.0111(6) 0.0006(6) O2 0.0202(7) 0.0345(9) 0.0161(7) 0.0012(6) 0.0048(5) 0.0017(6) C1 0.0235(10) 0.0227(10) 0.0166(9) -0.0001(8) 0.0083(8) -0.0013(8) C2 0.0219(10) 0.0158(9) 0.0194(10) -0.0013(7) 0.0070(8) -0.0012(7) C3 0.0207(10) 0.0185(9) 0.0205(10) -0.0012(7) 0.0073(8) -0.0013(7) C4 0.0220(10) 0.0168(9) 0.0216(10) -0.0011(8) 0.0046(8) -0.0016(8) C5 0.0225(10) 0.0280(11) 0.0297(11) -0.0032(9) 0.0093(8) -0.0016(8) C6 0.0191(10) 0.0329(12) 0.0364(12) -0.0011(10) 0.0044(9) 0.0009(9) C7 0.0262(11) 0.0321(12) 0.0266(11) 0.0014(9) -0.0015(9) 0.0007(9) C8 0.0253(10) 0.0345(12) 0.0220(11) 0.0026(9) 0.0042(9) -0.0002(9) C9 0.0206(10) 0.0200(10) 0.0225(10) 0.0006(8) 0.0048(8) -0.0005(8) C10 0.0218(10) 0.0181(9) 0.0159(9) -0.0004(7) 0.0036(7) -0.0004(7) C11 0.0211(10) 0.0184(9) 0.0156(9) 0.0000(7) 0.0051(7) 0.0002(7) C12 0.0194(9) 0.0176(9) 0.0172(9) -0.0003(7) 0.0044(7) -0.0003(7) C13 0.0189(9) 0.0194(10) 0.0192(9) -0.0037(7) 0.0037(7) -0.0001(7) C14 0.0255(10) 0.0224(10) 0.0211(10) -0.0002(8) 0.0028(8) -0.0009(8) C15 0.0251(11) 0.0290(11) 0.0282(11) 0.0026(9) -0.0005(9) 0.0030(9) C16 0.0182(10) 0.0331(12) 0.0319(12) -0.0046(9) 0.0016(8) 0.0019(9) C17 0.0231(10) 0.0317(12) 0.0231(10) -0.0015(9) 0.0079(8) -0.0014(9) C18 0.0221(10) 0.0278(11) 0.0183(9) 0.0001(8) 0.0056(8) 0.0014(8) C19 0.0144(9) 0.0306(11) 0.0159(9) -0.0001(8) 0.0035(7) 0.0000(8) C20 0.0207(10) 0.0334(12) 0.0181(10) -0.0029(8) 0.0038(8) 0.0020(8) C21 0.0218(10) 0.0476(14) 0.0213(11) -0.0105(10) 0.0041(8) 0.0036(10) C22 0.0200(10) 0.0613(17) 0.0155(10) -0.0035(10) 0.0055(8) -0.0019(10) C23 0.0220(10) 0.0488(15) 0.0195(10) 0.0075(10) 0.0026(8) -0.0054(10) C24 0.0223(10) 0.0337(12) 0.0200(10) 0.0028(9) 0.0055(8) 0.0007(9) _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 C1 1.323(3) . ? N1 C12 1.363(3) . ? O1 C3 1.225(2) . ? O2 C10 1.357(2) . ? O2 C9 1.385(2) . ? C1 C2 1.399(3) . ? C1 H1 0.9500 . ? C2 C10 1.393(3) . ? C2 C3 1.471(3) . ? C3 C4 1.475(3) . ? C4 C9 1.391(3) . ? C4 C5 1.406(3) . ? C5 C6 1.374(3) . ? C5 H5 0.9500 . ? C6 C7 1.397(3) . ? C6 H6 0.9500 . ? C7 C8 1.381(3) . ? C7 H7 0.9500 . ? C8 C9 1.393(3) . ? C8 H8 0.9500 . ? C10 C11 1.404(3) . ? C11 C12 1.408(3) . ? C11 C19 1.493(3) . ? C12 C13 1.487(3) . ? C13 C14 1.398(3) . ? C13 C18 1.399(3) . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 C17 1.393(3) . ? C16 H16 0.9500 . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.395(3) . ? C19 C24 1.397(3) . ? C20 C21 1.392(3) . ? C20 H20 0.9500 . ? C21 C22 1.386(4) . ? C21 H21 0.9500 . ? C22 C23 1.387(4) . ? C22 H22 0.9500 . ? C23 C24 1.394(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 C1 N1 C12 118.46(18) . . ? C10 O2 C9 119.10(16) . . ? N1 C1 C2 124.81(19) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? C10 C2 C1 116.08(18) . . ? C10 C2 C3 121.66(18) . . ? C1 C2 C3 122.25(18) . . ? O1 C3 C2 122.38(19) . . ? O1 C3 C4 123.80(19) . . ? C2 C3 C4 113.81(17) . . ? C9 C4 C5 118.04(19) . . ? C9 C4 C3 120.15(18) . . ? C5 C4 C3 121.79(19) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.7(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 118.4(2) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? O2 C9 C4 123.01(18) . . ? O2 C9 C8 114.90(18) . . ? C4 C9 C8 122.09(19) . . ? O2 C10 C2 122.11(18) . . ? O2 C10 C11 116.39(17) . . ? C2 C10 C11 121.48(18) . . ? C10 C11 C12 116.97(18) . . ? C10 C11 C19 118.67(17) . . ? C12 C11 C19 124.28(18) . . ? N1 C12 C11 122.08(18) . . ? N1 C12 C13 113.90(17) . . ? C11 C12 C13 124.02(18) . . ? C14 C13 C18 118.09(19) . . ? C14 C13 C12 118.53(18) . . ? C18 C13 C12 123.25(18) . . ? C15 C14 C13 121.4(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 120.2(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 119.2(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C13 120.5(2) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C20 C19 C24 119.53(19) . . ? C20 C19 C11 119.46(19) . . ? C24 C19 C11 121.01(19) . . ? C21 C20 C19 120.0(2) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 120.4(2) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 119.9(2) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C19 120.0(2) . . ? C23 C24 H24 120.0 . . ? C19 C24 H24 120.0 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.400 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.075