#============================================================================== data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 9 _journal_issue 4 _journal_year 2018 _journal_page_first 303 _journal_page_last 310 #=============================================================================== data_aadmab _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety CHNO _chemical_formula_sum 'C16 H16 N2 O2' _chemical_formula_weight 268.31 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.167(3) _cell_length_b 13.0454(8) _cell_length_c 15.377(3) _cell_angle_alpha 90.00 _cell_angle_beta 129.65(3) _cell_angle_gamma 90.00 _cell_volume 2805.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1181 _cell_measurement_theta_min 3.2674 _cell_measurement_theta_max 29.1211 _exptl_crystal_description rectangular _exptl_crystal_colour redish _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.80915 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5989 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 29.19 _reflns_number_total 3804 _reflns_number_gt 1651 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0512P)^2^+0.0475P] 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 3077 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.003 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 C13 C 0.45332(15) 0.59692(16) 0.34750(17) 0.0754(7) Uani 1 1 d . . . H13 H 0.5195 0.5924 0.3933 0.091 Uiso 1 1 calc R . . C2 C -0.34573(13) 0.71309(16) -0.17377(15) 0.0731(6) Uani 1 1 d . . . H2C H -0.4110 0.7130 -0.2035 0.110 Uiso 1 1 calc R . . H2A H -0.3438 0.7000 -0.2337 0.110 Uiso 1 1 calc R . . H2B H -0.3175 0.7787 -0.1406 0.110 Uiso 1 1 calc R . . C1 C -0.34868(15) 0.56346(17) -0.07676(18) 0.0819(7) Uani 1 1 d . . . H1A H -0.4133 0.5877 -0.1219 0.123 Uiso 1 1 calc R . . H1B H -0.3216 0.5601 0.0010 0.123 Uiso 1 1 calc R . . H1C H -0.3480 0.4964 -0.1020 0.123 Uiso 1 1 calc R . . O1 O 0.16869(11) 0.79251(10) 0.07460(13) 0.0922(5) Uani 1 1 d . . . H15 H 0.1468 0.7408 0.0810 0.138 Uiso 1 1 calc R . . O2 O 0.31076(12) 0.85593(12) 0.15272(15) 0.1074(6) Uani 1 1 d . . . C16 C 0.26236(17) 0.78601(16) 0.14255(18) 0.0734(6) Uani 1 1 d . . . H9 H 0.1297(13) 0.5119(15) 0.2046(16) 0.086(6) Uiso 1 1 d . . . N2 N 0.15531(10) 0.62616(10) 0.14563(10) 0.0530(4) Uani 1 1 d . . . C3 C -0.19763(13) 0.61672(13) -0.03236(13) 0.0524(5) Uani 1 1 d . . . C10 C 0.25514(12) 0.61181(12) 0.21312(13) 0.0512(5) Uani 1 1 d . . . C6 C 0.00102(13) 0.58612(12) 0.08820(13) 0.0520(5) Uani 1 1 d . . . C5 C -0.05251(14) 0.52092(13) 0.10101(14) 0.0564(5) Uani 1 1 d . . . H5 H -0.0218 0.4659 0.1507 0.068 Uiso 1 1 calc R . . C9 C 0.10129(14) 0.56948(13) 0.15184(14) 0.0532(5) Uani 1 1 d . . . C4 C -0.14811(14) 0.53431(14) 0.04380(14) 0.0587(5) Uani 1 1 d . . . H4 H -0.1807 0.4888 0.0552 0.070 Uiso 1 1 calc R . . C15 C 0.30705(13) 0.68954(12) 0.21071(14) 0.0551(5) Uani 1 1 d . . . N1 N -0.29257(12) 0.63344(12) -0.08790(12) 0.0648(5) Uani 1 1 d . . . C11 C 0.30452(13) 0.52668(14) 0.28256(15) 0.0620(5) Uani 1 1 d . . . H11 H 0.2710 0.4737 0.2839 0.074 Uiso 1 1 calc R . . C8 C -0.14496(13) 0.68171(14) -0.04781(15) 0.0609(5) Uani 1 1 d . . . H8 H -0.1758 0.7358 -0.0988 0.073 Uiso 1 1 calc R . . C7 C -0.04908(13) 0.66696(13) 0.01078(14) 0.0602(5) Uani 1 1 d . . . H7 H -0.0163 0.7117 -0.0010 0.072 Uiso 1 1 calc R . . C12 C 0.40210(15) 0.52070(16) 0.34868(15) 0.0724(6) Uani 1 1 d . . . H12 H 0.4340 0.4640 0.3951 0.087 Uiso 1 1 calc R . . C14 C 0.40578(15) 0.68055(15) 0.27763(17) 0.0693(6) Uani 1 1 d . . . H14 H 0.4402 0.7316 0.2753 0.083 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 C13 0.0610(12) 0.0737(14) 0.0767(14) -0.0161(11) 0.0370(11) 0.0011(11) C2 0.0683(13) 0.0803(15) 0.0674(12) 0.0050(10) 0.0417(11) 0.0012(10) C1 0.0793(14) 0.0890(16) 0.0935(15) -0.0056(11) 0.0626(13) -0.0185(11) O1 0.0927(11) 0.0634(9) 0.1219(12) 0.0344(8) 0.0691(10) 0.0154(8) O2 0.1243(13) 0.0665(10) 0.1677(16) 0.0219(9) 0.1100(12) -0.0039(9) C16 0.0916(16) 0.0521(12) 0.1019(16) 0.0069(10) 0.0736(14) 0.0013(11) N2 0.0576(9) 0.0459(8) 0.0510(9) -0.0019(6) 0.0325(8) -0.0033(7) C3 0.0627(11) 0.0552(10) 0.0454(9) -0.0074(7) 0.0373(9) -0.0114(8) C10 0.0636(12) 0.0413(9) 0.0472(10) -0.0070(7) 0.0347(9) -0.0028(8) C6 0.0658(12) 0.0460(9) 0.0482(9) -0.0008(7) 0.0383(9) -0.0053(8) C5 0.0748(13) 0.0476(10) 0.0505(10) 0.0032(7) 0.0416(10) -0.0054(9) C9 0.0661(13) 0.0450(10) 0.0474(10) -0.0013(8) 0.0356(10) -0.0033(9) C4 0.0771(13) 0.0529(11) 0.0610(11) -0.0021(8) 0.0510(11) -0.0136(9) C15 0.0663(12) 0.0447(10) 0.0659(11) -0.0073(7) 0.0476(10) -0.0021(8) N1 0.0655(10) 0.0707(10) 0.0639(10) 0.0017(7) 0.0440(9) -0.0075(8) C11 0.0668(12) 0.0503(10) 0.0575(11) -0.0012(8) 0.0343(10) -0.0055(9) C8 0.0692(12) 0.0580(11) 0.0618(11) 0.0137(8) 0.0447(10) -0.0004(9) C7 0.0679(12) 0.0571(11) 0.0622(11) 0.0070(8) 0.0447(10) -0.0082(9) C12 0.0705(13) 0.0630(12) 0.0565(12) -0.0015(9) 0.0278(11) 0.0078(10) C14 0.0772(14) 0.0605(13) 0.0883(14) -0.0180(10) 0.0612(12) -0.0088(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C13 C12 1.370(3) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C2 N1 1.459(2) . ? C2 H2C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C1 N1 1.458(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? O1 C16 1.314(2) . ? O1 H15 0.8200 . ? O2 C16 1.206(2) . ? C16 C15 1.502(2) . ? N2 C9 1.280(2) . ? N2 C10 1.414(2) . ? C3 N1 1.368(2) . ? C3 C4 1.411(2) . ? C3 C8 1.407(2) . ? C10 C11 1.399(2) . ? C10 C15 1.401(2) . ? C6 C5 1.397(3) . ? C6 C7 1.405(2) . ? C6 C9 1.431(3) . ? C5 C4 1.368(2) . ? C5 H5 0.9300 . ? C9 H9 0.977(19) . ? C4 H4 0.9300 . ? C15 C14 1.391(3) . ? C11 C12 1.372(3) . ? C11 H11 0.9300 . ? C8 C7 1.371(3) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C12 H12 0.9300 . ? C14 H14 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 C12 C13 C14 119.4(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? N1 C2 H2C 109.5 . . ? N1 C2 H2A 109.5 . . ? H2C C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2C C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C16 O1 H15 109.5 . . ? O2 C16 O1 121.44(19) . . ? O2 C16 C15 121.2(2) . . ? O1 C16 C15 117.27(19) . . ? C9 N2 C10 123.65(15) . . ? N1 C3 C4 121.42(17) . . ? N1 C3 C8 121.37(16) . . ? C4 C3 C8 117.20(18) . . ? C11 C10 C15 118.69(17) . . ? C11 C10 N2 124.27(17) . . ? C15 C10 N2 117.03(15) . . ? C5 C6 C7 116.33(18) . . ? C5 C6 C9 120.53(16) . . ? C7 C6 C9 123.14(18) . . ? C4 C5 C6 122.95(16) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? N2 C9 C6 124.28(16) . . ? N2 C9 H9 118.8(12) . . ? C6 C9 H9 116.8(12) . . ? C5 C4 C3 120.41(17) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C14 C15 C10 119.44(17) . . ? C14 C15 C16 117.03(19) . . ? C10 C15 C16 123.48(18) . . ? C3 N1 C1 121.63(17) . . ? C3 N1 C2 121.41(17) . . ? C1 N1 C2 116.35(17) . . ? C12 C11 C10 120.46(19) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C7 C8 C3 121.33(16) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C8 C7 C6 121.76(18) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C13 C12 C11 121.09(19) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C13 C14 C15 120.9(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? 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 C9 N2 C10 C11 9.4(3) . . . . ? C9 N2 C10 C15 -169.50(16) . . . . ? C7 C6 C5 C4 -1.1(3) . . . . ? C9 C6 C5 C4 178.84(16) . . . . ? C10 N2 C9 C6 176.73(15) . . . . ? C5 C6 C9 N2 -179.38(17) . . . . ? C7 C6 C9 N2 0.5(3) . . . . ? C6 C5 C4 C3 0.0(3) . . . . ? N1 C3 C4 C5 -177.99(16) . . . . ? C8 C3 C4 C5 1.3(3) . . . . ? C11 C10 C15 C14 -0.5(3) . . . . ? N2 C10 C15 C14 178.43(15) . . . . ? C11 C10 C15 C16 -177.88(17) . . . . ? N2 C10 C15 C16 1.1(3) . . . . ? O2 C16 C15 C14 -6.0(3) . . . . ? O1 C16 C15 C14 176.43(18) . . . . ? O2 C16 C15 C10 171.4(2) . . . . ? O1 C16 C15 C10 -6.1(3) . . . . ? C4 C3 N1 C1 -4.0(3) . . . . ? C8 C3 N1 C1 176.79(18) . . . . ? C4 C3 N1 C2 -174.65(16) . . . . ? C8 C3 N1 C2 6.1(3) . . . . ? C15 C10 C11 C12 1.3(3) . . . . ? N2 C10 C11 C12 -177.50(16) . . . . ? N1 C3 C8 C7 177.74(18) . . . . ? C4 C3 C8 C7 -1.5(3) . . . . ? C3 C8 C7 C6 0.5(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C9 C6 C7 C8 -179.09(17) . . . . ? C14 C13 C12 C11 -0.7(3) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C12 C13 C14 C15 1.6(3) . . . . ? C10 C15 C14 C13 -1.0(3) . . . . ? C16 C15 C14 C13 176.58(18) . . . . ? _diffrn_measured_fraction_theta_max 0.809 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.156 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032