#============================================================================== data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 12 _journal_issue 2 _journal_year 2021 _journal_page_first 133 _journal_page_last 146 #============================================================================== data_annamalai_cba_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 N O4' _chemical_formula_sum 'C18 H13 N O4' _chemical_formula_weight 307.29 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.399(5) _cell_length_b 5.876(5) _cell_length_c 21.859(5) _cell_angle_alpha 90.000 _cell_angle_beta 91.060(5) _cell_angle_gamma 90.000 _cell_volume 1463.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3669 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 28.49 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 'Bruker SMART APEXII area-detector diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13555 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.49 _reflns_number_total 3669 _reflns_number_gt 2379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'APEX2' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 2012)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2009)' _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^)+(0.0776P)^2^+0.1746P] 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 3669 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1506 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.006 _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 C1 C 0.73945(11) -0.1565(3) 0.72576(6) 0.0450(3) Uani 1 1 d . . . C2 C 0.76062(14) -0.3314(3) 0.68504(7) 0.0550(4) Uani 1 1 d . . . H2 H 0.7077 -0.4509 0.6803 0.066 Uiso 1 1 calc R . . C3 C 0.86185(14) -0.3244(3) 0.65164(7) 0.0578(4) Uani 1 1 d . . . H3 H 0.8781 -0.4422 0.6247 0.069 Uiso 1 1 calc R . . C4 C 0.93996(13) -0.1441(3) 0.65765(7) 0.0558(4) Uani 1 1 d . . . H4 H 1.0080 -0.1420 0.6349 0.067 Uiso 1 1 calc R . . C5 C 0.91693(12) 0.0305(3) 0.69702(7) 0.0524(4) Uani 1 1 d . . . H5 H 0.9686 0.1526 0.7003 0.063 Uiso 1 1 calc R . . C6 C 0.81544(12) 0.0261(3) 0.73254(6) 0.0446(3) Uani 1 1 d . . . C7 C 0.78492(12) 0.1999(3) 0.77497(6) 0.0467(4) Uani 1 1 d . . . H7 H 0.8337 0.3260 0.7791 0.056 Uiso 1 1 calc R . . C8 C 0.68782(11) 0.1879(3) 0.80933(6) 0.0444(3) Uani 1 1 d . . . C9 C 0.60938(13) -0.0078(3) 0.80227(7) 0.0490(4) Uani 1 1 d . . . C10 C 0.66176(12) 0.3692(3) 0.85462(6) 0.0475(4) Uani 1 1 d . . . C11 C 0.54081(14) 0.4126(3) 0.87703(9) 0.0715(5) Uani 1 1 d . . . H11A H 0.5328 0.3470 0.9170 0.107 Uiso 1 1 calc R . . H11B H 0.4845 0.3450 0.8494 0.107 Uiso 1 1 calc R . . H11C H 0.5274 0.5736 0.8792 0.107 Uiso 1 1 calc R . . C12 C 0.81262(13) 0.8052(3) 0.92319(7) 0.0538(4) Uani 1 1 d . . . C13 C 0.78102(12) 0.9731(3) 0.97050(6) 0.0483(4) Uani 1 1 d . . . C14 C 0.85986(14) 1.1473(3) 0.98306(7) 0.0584(4) Uani 1 1 d . . . H14 H 0.9304 1.1542 0.9624 0.070 Uiso 1 1 calc R . . C15 C 0.83393(16) 1.3105(3) 1.02608(8) 0.0658(5) Uani 1 1 d . . . H15 H 0.8867 1.4280 1.0341 0.079 Uiso 1 1 calc R . . C16 C 0.73072(16) 1.3001(3) 1.05710(8) 0.0668(5) Uani 1 1 d . . . H16 H 0.7135 1.4109 1.0860 0.080 Uiso 1 1 calc R . . C17 C 0.65250(15) 1.1266(4) 1.04576(8) 0.0693(5) Uani 1 1 d . . . H17 H 0.5829 1.1195 1.0672 0.083 Uiso 1 1 calc R . . C18 C 0.67710(13) 0.9625(3) 1.00247(7) 0.0587(4) Uani 1 1 d . . . H18 H 0.6241 0.8452 0.9948 0.070 Uiso 1 1 calc R . . N1 N 0.75283(11) 0.4832(3) 0.87012(6) 0.0562(4) Uani 1 1 d . . . O1 O 0.63888(8) -0.16831(18) 0.75939(5) 0.0534(3) Uani 1 1 d . . . O2 O 0.52140(10) -0.0448(2) 0.82990(6) 0.0692(4) Uani 1 1 d . . . O3 O 0.72259(9) 0.6597(2) 0.91194(5) 0.0585(3) Uani 1 1 d . . . O4 O 0.90366(11) 0.7997(3) 0.89716(7) 0.0910(5) Uani 1 1 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 C1 0.0401(7) 0.0501(9) 0.0450(7) 0.0040(6) 0.0050(5) 0.0019(6) C2 0.0542(8) 0.0513(10) 0.0598(9) -0.0036(7) 0.0045(7) -0.0031(7) C3 0.0580(9) 0.0623(11) 0.0532(9) -0.0092(7) 0.0084(7) 0.0062(8) C4 0.0447(8) 0.0740(12) 0.0491(8) -0.0035(8) 0.0087(6) 0.0042(8) C5 0.0429(7) 0.0646(10) 0.0499(8) -0.0022(7) 0.0061(6) -0.0060(7) C6 0.0408(7) 0.0514(9) 0.0418(7) 0.0013(6) 0.0023(5) 0.0006(6) C7 0.0425(7) 0.0501(9) 0.0474(7) -0.0003(6) 0.0017(6) -0.0027(6) C8 0.0417(7) 0.0482(9) 0.0433(7) 0.0029(6) 0.0014(6) 0.0058(6) C9 0.0455(7) 0.0509(9) 0.0510(8) 0.0065(7) 0.0091(6) 0.0047(7) C10 0.0452(7) 0.0499(9) 0.0475(8) 0.0041(6) 0.0042(6) 0.0093(7) C11 0.0549(9) 0.0644(12) 0.0959(13) -0.0173(10) 0.0233(9) 0.0016(8) C12 0.0475(8) 0.0621(11) 0.0519(8) -0.0041(7) 0.0037(6) 0.0073(7) C13 0.0462(8) 0.0568(10) 0.0420(7) -0.0001(6) 0.0007(6) 0.0092(7) C14 0.0576(9) 0.0654(11) 0.0525(9) 0.0017(8) 0.0075(7) -0.0007(8) C15 0.0741(11) 0.0606(12) 0.0625(10) -0.0045(8) -0.0017(8) -0.0028(9) C16 0.0742(11) 0.0700(13) 0.0560(9) -0.0137(8) 0.0010(8) 0.0135(10) C17 0.0562(9) 0.0881(14) 0.0639(10) -0.0139(10) 0.0117(8) 0.0106(10) C18 0.0477(8) 0.0693(12) 0.0593(9) -0.0102(8) 0.0061(7) 0.0010(8) N1 0.0479(7) 0.0671(9) 0.0537(7) -0.0157(6) 0.0025(5) 0.0111(6) O1 0.0476(6) 0.0517(7) 0.0615(6) -0.0028(5) 0.0153(5) -0.0056(5) O2 0.0597(7) 0.0628(8) 0.0861(8) 0.0017(6) 0.0321(6) -0.0034(6) O3 0.0486(6) 0.0689(8) 0.0582(6) -0.0188(6) 0.0056(5) 0.0074(5) O4 0.0653(8) 0.1036(12) 0.1052(10) -0.0412(9) 0.0363(7) -0.0096(8) _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 C1 O1 1.3749(16) . ? C1 C6 1.385(2) . ? C1 C2 1.384(2) . ? C2 C3 1.378(2) . ? C2 H2 0.9300 . ? C3 C4 1.389(2) . ? C3 H3 0.9300 . ? C4 C5 1.368(2) . ? C4 H4 0.9300 . ? C5 C6 1.4054(19) . ? C5 H5 0.9300 . ? C6 C7 1.427(2) . ? C7 C8 1.3508(19) . ? C7 H7 0.9300 . ? C8 C9 1.463(2) . ? C8 C10 1.488(2) . ? C9 O2 1.2001(17) . ? C9 O1 1.3757(19) . ? C10 N1 1.276(2) . ? C10 C11 1.494(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O4 1.1932(18) . ? C12 O3 1.355(2) . ? C12 C13 1.479(2) . ? C13 C14 1.386(2) . ? C13 C18 1.388(2) . ? C14 C15 1.379(2) . ? C14 H14 0.9300 . ? C15 C16 1.370(2) . ? C15 H15 0.9300 . ? C16 C17 1.374(3) . ? C16 H16 0.9300 . ? C17 C18 1.384(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N1 O3 1.4288(17) . ? 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 O1 C1 C6 120.51(13) . . ? O1 C1 C2 117.62(13) . . ? C6 C1 C2 121.87(13) . . ? C3 C2 C1 118.47(15) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 120.95(15) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.12(14) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.23(15) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 118.34(14) . . ? C1 C6 C7 117.67(13) . . ? C5 C6 C7 123.99(14) . . ? C8 C7 C6 122.44(14) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C7 C8 C9 119.18(13) . . ? C7 C8 C10 120.56(14) . . ? C9 C8 C10 120.25(13) . . ? O2 C9 O1 115.84(14) . . ? O2 C9 C8 127.16(15) . . ? O1 C9 C8 117.00(12) . . ? N1 C10 C8 112.40(13) . . ? N1 C10 C11 125.08(15) . . ? C8 C10 C11 122.50(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 O3 123.98(15) . . ? O4 C12 C13 125.23(16) . . ? O3 C12 C13 110.77(13) . . ? C14 C13 C18 119.33(15) . . ? C14 C13 C12 117.76(14) . . ? C18 C13 C12 122.91(15) . . ? C15 C14 C13 120.14(15) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.23(17) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.28(17) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 120.10(16) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 119.91(17) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C10 N1 O3 110.26(12) . . ? C9 O1 C1 123.13(12) . . ? C12 O3 N1 112.54(11) . . ? 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 O1 C1 C2 C3 -179.00(13) . . . . ? C6 C1 C2 C3 1.6(2) . . . . ? C1 C2 C3 C4 -1.3(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? O1 C1 C6 C5 -179.86(12) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? O1 C1 C6 C7 -0.4(2) . . . . ? C2 C1 C6 C7 178.97(13) . . . . ? C4 C5 C6 C1 -1.0(2) . . . . ? C4 C5 C6 C7 179.59(14) . . . . ? C1 C6 C7 C8 2.0(2) . . . . ? C5 C6 C7 C8 -178.60(14) . . . . ? C6 C7 C8 C9 -1.1(2) . . . . ? C6 C7 C8 C10 177.79(13) . . . . ? C7 C8 C9 O2 178.72(15) . . . . ? C10 C8 C9 O2 -0.2(2) . . . . ? C7 C8 C9 O1 -1.3(2) . . . . ? C10 C8 C9 O1 179.81(11) . . . . ? C7 C8 C10 N1 -20.8(2) . . . . ? C9 C8 C10 N1 158.13(14) . . . . ? C7 C8 C10 C11 157.53(16) . . . . ? C9 C8 C10 C11 -23.5(2) . . . . ? O4 C12 C13 C14 4.4(3) . . . . ? O3 C12 C13 C14 -174.05(13) . . . . ? O4 C12 C13 C18 -175.36(17) . . . . ? O3 C12 C13 C18 6.2(2) . . . . ? C18 C13 C14 C15 -1.2(2) . . . . ? C12 C13 C14 C15 178.99(14) . . . . ? C13 C14 C15 C16 0.7(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C15 C16 C17 C18 -0.6(3) . . . . ? C16 C17 C18 C13 0.0(3) . . . . ? C14 C13 C18 C17 0.9(2) . . . . ? C12 C13 C18 C17 -179.36(15) . . . . ? C8 C10 N1 O3 178.01(11) . . . . ? C11 C10 N1 O3 -0.3(2) . . . . ? O2 C9 O1 C1 -177.10(14) . . . . ? C8 C9 O1 C1 2.9(2) . . . . ? C6 C1 O1 C9 -2.1(2) . . . . ? C2 C1 O1 C9 178.51(13) . . . . ? O4 C12 O3 N1 6.3(2) . . . . ? C13 C12 O3 N1 -175.20(12) . . . . ? C10 N1 O3 C12 -171.35(13) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.180 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.032