#============================================================================= data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 15 _journal_issue 1 _journal_year 2024 _journal_page_first 39 _journal_page_last 49 #============================================================================= data_ms3ov_rt _audit_creation_date 2023-11-08 _audit_creation_method ; Olex2 1.3-beta (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_contact_author_address ? _audit_contact_author_email ? _audit_contact_author_name '' _audit_contact_author_phone ? _publ_contact_author_id_orcid ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. ; _chemical_name_common ? _chemical_name_systematic C14H12N2O2 _chemical_formula_moiety 'C14 H12 N2 O2' _chemical_formula_sum 'C14 H12 N2 O2' _chemical_formula_weight 240.26 _chemical_melting_point ? 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' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7190(10) _cell_length_b 12.3492(15) _cell_length_c 12.2568(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.138(8) _cell_angle_gamma 90.00 _cell_volume 1165.3(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1793 _cell_measurement_temperature 298.0(2) _cell_measurement_theta_max 22.5070 _cell_measurement_theta_min 3.0160 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_unetI/netI 0.0315 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 12383 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.02 _diffrn_ambient_temperature 298.0(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -69.00 118.80 0.30 35.00 -- 29.89 54.00 -90.00 626 2 \w -69.00 118.80 0.30 35.00 -- 29.89 54.00-180.00 626 3 \w -68.00 112.00 0.30 35.00 -- 29.89 54.00 150.00 600 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1712 _reflns_number_total 2646 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 97-2 (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.262 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2646 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0594 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1060P)^2^+0.1681P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1676 _refine_ls_wR_factor_ref 0.1980 _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. ; _olex2_refinement_description ; 1. Others Fixed Uiso: H1(0.098) H1A(0.065) H1B(0.136) H1C(0.136) H1D(0.136) H3(0.073) H4(0.075) H5(0.067) H10(0.078) H11(0.085) H12(0.081) H13(0.073) Fixed X: H1(0.3103) H1A(0.5729) H1B(-0.2743) H1C(-0.3048) H1D(-0.1959) H3(- 0.1311) H4(0.0442) H5(0.303) H10(0.7309) H11(0.9908) H12(1.0755) H13(0.9027) Fixed Y: H1(0.3017) H1A(0.2692) H1B(0.0974) H1C(0.129) H1D(0.0256) H3(0.0851) H4(0.1052) H5(0.1953) H10(0.4765) H11(0.5362) H12(0.4835) H13(0.3734) Fixed Z: H1(0.5209) H1A(0.8493) H1B(0.4312) H1C(0.5522) H1D(0.5281) H3(0.7058) H4(0.8672) H5(0.8665) H10(0.5133) H11(0.5996) H12(0.7756) H13(0.874) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.2197(2) 0.26712(14) 0.51196(11) 0.0656(5) Uani 1 1 d . . . H1 H 0.3103 0.3017 0.5209 0.098 Uiso 1 1 calc R . . O2 O -0.0699(2) 0.16167(15) 0.51052(13) 0.0730(5) Uani 1 1 d . . . N1 N 0.5771(2) 0.29826(15) 0.78579(14) 0.0543(5) Uani 1 1 d . . . H1A H 0.5729 0.2692 0.8493 0.065 Uiso 1 1 calc R . . N2 N 0.4981(2) 0.34469(15) 0.61388(13) 0.0542(5) Uani 1 1 d . . . C1 C -0.2237(4) 0.0983(3) 0.5050(2) 0.0908(10) Uani 1 1 d . . . H1B H -0.2743 0.0974 0.4312 0.136 Uiso 1 1 calc R . . H1C H -0.3048 0.1290 0.5522 0.136 Uiso 1 1 calc R . . H1D H -0.1959 0.0256 0.5281 0.136 Uiso 1 1 calc R . . C2 C 0.0230(3) 0.16737(18) 0.61083(17) 0.0554(6) Uani 1 1 d . . . C3 C -0.0270(3) 0.12294(19) 0.70557(18) 0.0605(6) Uani 1 1 d . . . H3 H -0.1311 0.0851 0.7058 0.073 Uiso 1 1 calc R . . C4 C 0.0789(3) 0.13445(19) 0.80233(18) 0.0621(6) Uani 1 1 d . . . H4 H 0.0442 0.1052 0.8672 0.075 Uiso 1 1 calc R . . C5 C 0.2332(3) 0.18851(18) 0.80180(17) 0.0558(6) Uani 1 1 d . . . H5 H 0.3030 0.1953 0.8665 0.067 Uiso 1 1 calc R . . C6 C 0.2881(3) 0.23383(16) 0.70531(15) 0.0494(5) Uani 1 1 d . . . C7 C 0.1793(3) 0.22416(16) 0.60880(15) 0.0502(5) Uani 1 1 d . . . C8 C 0.4521(3) 0.29161(16) 0.70172(15) 0.0495(5) Uani 1 1 d . . . C9 C 0.6601(3) 0.38942(17) 0.64265(16) 0.0524(5) Uani 1 1 d . . . C10 C 0.7639(3) 0.4559(2) 0.58473(19) 0.0652(6) Uani 1 1 d . . . H10 H 0.7309 0.4765 0.5133 0.078 Uiso 1 1 calc R . . C11 C 0.9189(3) 0.4908(2) 0.6367(2) 0.0706(7) Uani 1 1 d . . . H11 H 0.9908 0.5362 0.5996 0.085 Uiso 1 1 calc R . . C12 C 0.9696(3) 0.4593(2) 0.7436(2) 0.0672(7) Uani 1 1 d . . . H12 H 1.0755 0.4835 0.7756 0.081 Uiso 1 1 calc R . . C13 C 0.8683(3) 0.39395(19) 0.80269(18) 0.0610(6) Uani 1 1 d . . . H13 H 0.9027 0.3734 0.8740 0.073 Uiso 1 1 calc R . . C14 C 0.7110(3) 0.35951(17) 0.75112(17) 0.0515(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 O1 0.0713(11) 0.0885(12) 0.0353(8) 0.0080(7) -0.0087(7) -0.0201(8) O2 0.0708(11) 0.0963(12) 0.0485(9) 0.0072(8) -0.0202(7) -0.0251(9) N1 0.0544(10) 0.0682(11) 0.0384(9) 0.0057(8) -0.0099(7) -0.0058(8) N2 0.0552(10) 0.0682(11) 0.0383(9) 0.0013(7) -0.0040(7) -0.0060(8) C1 0.0816(19) 0.114(2) 0.0727(17) 0.0056(16) -0.0245(14) -0.0357(17) C2 0.0582(13) 0.0620(12) 0.0436(12) 0.0007(9) -0.0122(9) -0.0030(9) C3 0.0621(13) 0.0659(13) 0.0519(13) 0.0065(10) -0.0055(10) -0.0098(11) C4 0.0641(14) 0.0760(15) 0.0452(12) 0.0117(10) -0.0032(10) -0.0053(11) C5 0.0580(13) 0.0669(13) 0.0411(11) 0.0030(9) -0.0067(9) -0.0013(10) C6 0.0532(12) 0.0543(11) 0.0391(11) 0.0008(8) -0.0066(8) -0.0002(8) C7 0.0560(12) 0.0569(12) 0.0365(10) -0.0003(8) -0.0042(8) -0.0010(9) C8 0.0540(12) 0.0569(11) 0.0364(10) -0.0012(8) -0.0043(8) 0.0016(9) C9 0.0520(12) 0.0645(12) 0.0400(11) -0.0030(9) -0.0020(8) -0.0026(9) C10 0.0662(14) 0.0848(16) 0.0441(12) 0.0013(11) 0.0000(10) -0.0140(12) C11 0.0643(15) 0.0907(17) 0.0568(15) -0.0009(12) 0.0042(11) -0.0181(12) C12 0.0557(13) 0.0820(16) 0.0620(15) -0.0029(11) -0.0091(11) -0.0102(11) C13 0.0578(13) 0.0721(14) 0.0509(13) 0.0012(10) -0.0108(10) -0.0015(10) C14 0.0502(11) 0.0573(11) 0.0456(11) -0.0009(9) -0.0049(8) 0.0038(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 O1 H1 0.8200 . ? O1 C7 1.357(2) . ? O2 C1 1.419(3) . ? O2 C2 1.380(2) . ? N1 H1A 0.8600 . ? N1 C8 1.362(2) . ? N1 C14 1.372(3) . ? N2 C8 1.330(3) . ? N2 C9 1.389(3) . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 H1D 0.9600 . ? C2 C3 1.365(3) . ? C2 C7 1.398(3) . ? C3 H3 0.9300 . ? C3 C4 1.398(3) . ? C4 H4 0.9300 . ? C4 C5 1.366(3) . ? C5 H5 0.9300 . ? C5 C6 1.401(3) . ? C6 C7 1.405(3) . ? C6 C8 1.457(3) . ? C9 C10 1.380(3) . ? C9 C14 1.408(3) . ? C10 H10 0.9300 . ? C10 C11 1.383(3) . ? C11 H11 0.9300 . ? C11 C12 1.396(3) . ? C12 H12 0.9300 . ? C12 C13 1.367(3) . ? C13 H13 0.9300 . ? C13 C14 1.395(3) . ? 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 C7 O1 H1 109.5 . . ? C2 O2 C1 116.70(19) . . ? C8 N1 H1A 126.1 . . ? C8 N1 C14 107.87(17) . . ? C14 N1 H1A 126.1 . . ? C8 N2 C9 106.17(16) . . ? O2 C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? O2 C1 H1D 109.5 . . ? H1B C1 H1C 109.5 . . ? H1B C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? O2 C2 C7 113.81(19) . . ? C3 C2 O2 125.3(2) . . ? C3 C2 C7 120.94(19) . . ? C2 C3 H3 120.1 . . ? C2 C3 C4 119.8(2) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 119.5 . . ? C4 C5 C6 121.06(19) . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 118.56(19) . . ? C5 C6 C8 122.49(17) . . ? C7 C6 C8 118.94(18) . . ? O1 C7 C2 117.69(17) . . ? O1 C7 C6 122.85(19) . . ? C2 C7 C6 119.46(19) . . ? N1 C8 C6 125.20(18) . . ? N2 C8 N1 111.50(18) . . ? N2 C8 C6 123.30(17) . . ? N2 C9 C14 108.67(18) . . ? C10 C9 N2 130.69(19) . . ? C10 C9 C14 120.60(19) . . ? C9 C10 H10 121.2 . . ? C9 C10 C11 117.7(2) . . ? C11 C10 H10 121.2 . . ? C10 C11 H11 119.3 . . ? C10 C11 C12 121.3(2) . . ? C12 C11 H11 119.3 . . ? C11 C12 H12 119.0 . . ? C13 C12 C11 122.0(2) . . ? C13 C12 H12 119.0 . . ? C12 C13 H13 121.5 . . ? C12 C13 C14 116.9(2) . . ? C14 C13 H13 121.5 . . ? N1 C14 C9 105.78(17) . . ? N1 C14 C13 132.7(2) . . ? C13 C14 C9 121.5(2) . . ? 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 O2 C2 C3 C4 -179.9(2) . . . . ? O2 C2 C7 O1 0.8(3) . . . . ? O2 C2 C7 C6 -178.63(18) . . . . ? N2 C9 C10 C11 178.1(2) . . . . ? N2 C9 C14 N1 -0.7(2) . . . . ? N2 C9 C14 C13 -179.31(19) . . . . ? C1 O2 C2 C3 -4.4(4) . . . . ? C1 O2 C2 C7 175.4(2) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C3 C2 C7 O1 -179.3(2) . . . . ? C3 C2 C7 C6 1.2(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C7 1.1(3) . . . . ? C4 C5 C6 C8 -179.7(2) . . . . ? C5 C6 C7 O1 178.7(2) . . . . ? C5 C6 C7 C2 -1.8(3) . . . . ? C5 C6 C8 N1 7.5(3) . . . . ? C5 C6 C8 N2 -172.8(2) . . . . ? C7 C2 C3 C4 0.2(4) . . . . ? C7 C6 C8 N1 -173.34(19) . . . . ? C7 C6 C8 N2 6.4(3) . . . . ? C8 N1 C14 C9 0.2(2) . . . . ? C8 N1 C14 C13 178.6(2) . . . . ? C8 N2 C9 C10 -176.8(2) . . . . ? C8 N2 C9 C14 1.0(2) . . . . ? C8 C6 C7 O1 -0.5(3) . . . . ? C8 C6 C7 C2 178.94(19) . . . . ? C9 N2 C8 N1 -0.9(2) . . . . ? C9 N2 C8 C6 179.37(18) . . . . ? C9 C10 C11 C12 0.5(4) . . . . ? C10 C9 C14 N1 177.4(2) . . . . ? C10 C9 C14 C13 -1.3(3) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C11 C12 C13 C14 0.2(4) . . . . ? C12 C13 C14 N1 -177.3(2) . . . . ? C12 C13 C14 C9 0.9(3) . . . . ? C14 N1 C8 N2 0.4(2) . . . . ? C14 N1 C8 C6 -179.79(19) . . . . ? C14 C9 C10 C11 0.5(4) . . . . ? _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ;