#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200562.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200562 loop_ _publ_author_name 'Rybakov, Victor B.' 'Chernyshev, Vladimir V.' 'Ukrainets, Igor V.' 'Bezugly, Peter A.' 'Sidorenko, Lyudmila V.' 'Skaif, Nicola' _publ_section_title ; 4-(4-Ethoxyphenylamino)-2-oxo-1,2-dihydroquinoline ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o721 _journal_page_last o722 _journal_paper_doi 10.1107/S160053680101100X _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C17 H16 N2 O2' _chemical_formula_sum 'C17 H16 N2 O2' _chemical_formula_weight 280.32 _chemical_melting_point 835.1(10) _chemical_name_systematic ' 4-(4-ethoxyphenylamino)-2-oxo-1,2-dihydroquinoline' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_type_scat_source 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_angle_alpha 105.85(4) _cell_angle_beta 93.44(3) _cell_angle_gamma 106.89(3) _cell_formula_units_Z 2 _cell_length_a 7.075(3) _cell_length_b 8.783(5) _cell_length_c 12.469(5) _cell_measurement_reflns_used 22 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 17.7 _cell_measurement_theta_min 15.7 _cell_volume 705.0(6) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'WinGX98 (Farrugia, 1998a)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1998b)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .017 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2956 _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 1.72 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 125 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .09 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 296 _exptl_crystal_size_max .43 _exptl_crystal_size_mid .33 _exptl_crystal_size_min .18 _refine_diff_density_max .212 _refine_diff_density_min -.198 _refine_ls_extinction_coef .029(5) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997a)' _refine_ls_goodness_of_fit_ref 1.10 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 255 _refine_ls_number_reflns 2765 _refine_ls_R_factor_gt .046 _refine_ls_shift/su_max .049 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .104 _reflns_number_gt 1912 _reflns_number_total 2765 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ya6028.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '561-563_C' was changed to '835.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '561-563_C' was changed to '835.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2200562 _cod_database_fobs_code 2200562 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol N1 .3302(2) .5856(2) .57407(13) .0343(4) Uani N C2 .3134(2) .4534(2) .61421(15) .0333(4) Uani C O21 .4355(2) .3743(2) .59408(12) .0499(4) Uani O C3 .1540(3) .4123(2) .67582(15) .0334(4) Uani C C4 .0216(2) .4986(2) .69438(15) .0318(4) Uani C N41 -.1416(2) .4544(2) .7477(2) .0443(4) Uani N C5 .0523(2) .6465(2) .65758(14) .0320(4) Uani C C6 -.0586(3) .7563(3) .6831(2) .0449(5) Uani C C7 -.0175(3) .8956(3) .6475(2) .0498(5) Uani C C8 .1360(3) .9295(2) .5841(2) .0423(5) Uani C C9 .2469(3) .8248(2) .5577(2) .0356(4) Uani C C10 .2084(2) .6839(2) .59548(14) .0296(4) Uani C C11 -.1855(3) .3181(2) .7926(2) .0363(4) Uani C C12 -.3678(3) .1944(2) .7587(2) .0404(5) Uani C C13 -.4152(3) .0619(2) .8031(2) .0413(5) Uani C C14 -.2768(3) .0526(2) .8821(2) .0375(4) Uani C O141 -.3045(2) -.0749(2) .92861(11) .0489(4) Uani O C15 -.0944(3) .1797(2) .9191(2) .0428(5) Uani C C16 -.0510(3) .3111(2) .8759(2) .0437(5) Uani C C17 -.4821(3) -.2150(3) .8858(2) .0453(5) Uani C C18 -.4656(4) -.3439(3) .9401(3) .0581(6) Uani C H1 .425(3) .604(3) .5253(18) .056(6) Uiso H H3 .143(3) .320(2) .7003(14) .036(5) Uiso H H6 -.158(3) .739(3) .7323(17) .057(6) Uiso H H7 -.087(3) .967(3) .6655(19) .069(7) Uiso H H8 .163(3) 1.030(3) .5608(16) .049(5) Uiso H H9 .355(3) .843(2) .5142(15) .040(5) Uiso H H12 -.458(3) .204(2) .7058(17) .050(6) Uiso H H13 -.546(3) -.024(3) .7808(16) .049(5) Uiso H H15 -.004(3) .174(3) .9774(17) .050(5) Uiso H H16 .072(3) .405(3) .9048(16) .052(6) Uiso H H41 -.243(4) .478(3) .7251(19) .066(7) Uiso H H171 -.598(3) -.177(2) .9037(16) .044(5) Uiso H H172 -.486(3) -.254(3) .8010(19) .056(6) Uiso H H181 -.459(4) -.303(3) 1.020(2) .083(9) Uiso H H182 -.339(4) -.375(3) .926(2) .093(9) Uiso H H183 -.580(4) -.442(4) .915(2) .100(10) Uiso H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol N1 .0333(8) .0380(9) .0429(9) .0171(7) .0153(7) .0220(7) N C2 .0334(9) .0364(10) .0385(10) .0164(8) .0095(8) .0184(8) C O21 .0516(8) .0618(9) .0684(10) .0396(7) .0321(7) .0429(8) O C3 .0370(9) .0302(9) .0398(10) .0131(8) .0103(8) .0179(8) C C4 .0304(9) .0312(9) .0370(10) .0098(7) .0084(7) .0147(8) C N41 .0379(9) .0477(10) .0671(12) .0228(8) .0255(8) .0356(9) N C5 .0319(9) .0307(9) .0364(10) .0118(7) .0065(7) .0127(8) C C6 .0474(11) .0450(11) .0562(13) .0255(9) .0221(10) .0231(10) C C7 .0575(13) .0410(11) .0658(14) .0309(10) .0167(11) .0224(11) C C8 .0508(12) .0332(10) .0479(12) .0157(9) .0038(9) .0187(9) C C9 .0373(10) .0358(10) .0370(10) .0110(8) .0048(8) .0173(8) C C10 .0304(9) .0289(9) .0309(9) .0097(7) .0033(7) .0110(7) C C11 .0357(10) .0383(10) .0446(11) .0158(8) .0173(8) .0213(9) C C12 .0333(10) .0484(11) .0458(11) .0133(8) .0055(8) .0240(9) C C13 .0337(10) .0414(11) .0457(11) .0032(8) .0008(8) .0189(9) C C14 .0395(10) .0364(10) .0371(10) .0077(8) .0062(8) .0166(8) C O141 .0471(8) .0431(8) .0535(9) -.0003(6) -.0060(6) .0284(7) O C15 .0361(10) .0462(11) .0442(12) .0040(9) -.0010(9) .0224(10) C C16 .0339(10) .0425(11) .0508(12) .0018(9) .0047(9) .0196(9) C C17 .0384(11) .0417(11) .0541(14) .0025(9) .0061(9) .0230(10) C C18 .058(2) .0477(13) .071(2) .0060(12) .0079(13) .0344(13) C loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 N1 C10 123.42(15) yes C2 N1 H1 116.8(12) no C10 N1 H1 119.6(12) no O21 C2 N1 119.2(2) yes O21 C2 C3 123.8(2) yes N1 C2 C3 117.00(15) yes C4 C3 C2 122.4(2) yes C4 C3 H3 121.9(11) no C2 C3 H3 115.7(11) no C3 C4 N41 123.4(2) yes C3 C4 C5 119.2(2) yes N41 C4 C5 117.42(15) yes C4 N41 C11 123.7(2) yes C4 N41 H41 114.7(15) no C11 N41 H41 115.3(15) no C6 C5 C10 117.9(2) yes C6 C5 C4 124.6(2) yes C10 C5 C4 117.49(15) yes C7 C6 C5 121.2(2) yes C7 C6 H6 119.6(12) no C5 C6 H6 119.0(12) no C6 C7 C8 120.3(2) yes C6 C7 H7 120.7(14) no C8 C7 H7 119.0(14) no C9 C8 C7 120.0(2) yes C9 C8 H8 121.6(12) no C7 C8 H8 118.4(11) no C8 C9 C10 120.1(2) yes C8 C9 H9 123.3(11) no C10 C9 H9 116.6(10) no N1 C10 C5 120.22(15) yes N1 C10 C9 119.2(2) yes C5 C10 C9 120.5(2) yes C12 C11 C16 118.6(2) yes C12 C11 N41 120.2(2) yes C16 C11 N41 121.1(2) yes C11 C12 C13 121.1(2) yes C11 C12 H12 117.5(12) no C13 C12 H12 121.3(12) no C14 C13 C12 119.7(2) yes C14 C13 H13 119.2(11) no C12 C13 H13 121.1(11) no O141 C14 C13 124.7(2) yes O141 C14 C15 115.8(2) yes C13 C14 C15 119.5(2) yes C14 O141 C17 117.59(14) yes C16 C15 C14 120.2(2) yes C16 C15 H15 122.0(12) no C14 C15 H15 117.8(12) no C15 C16 C11 120.8(2) yes C15 C16 H16 120.9(11) no C11 C16 H16 118.2(11) no O141 C17 C18 107.2(2) yes O141 C17 H171 108.5(11) no C18 C17 H171 112.3(11) no O141 C17 H172 106.1(11) no C18 C17 H172 112.6(12) no H171 C17 H172 109.8(16) no C17 C18 H181 111.0(16) no C17 C18 H182 111.3(15) no H181 C18 H182 107(2) no C17 C18 H183 111.8(16) no H181 C18 H183 106(2) no H182 C18 H183 110(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 . . 1.363(2) yes N1 C10 . . 1.375(2) yes C2 O21 . . 1.254(2) yes C2 C3 . . 1.419(2) yes C3 C4 . . 1.359(2) yes C3 H3 . . .93(2) no C4 N41 . . 1.378(2) yes C4 C5 . . 1.455(2) yes N41 C11 . . 1.419(2) yes N41 H41 . . .86(2) no C5 C6 . . 1.396(3) yes C5 C10 . . 1.400(2) yes C6 C7 . . 1.373(3) yes C6 H6 . . .96(2) no C7 C8 . . 1.391(3) yes C7 H7 . . .90(2) no C8 C9 . . 1.362(3) yes C8 H8 . . .98(2) no C9 C10 . . 1.402(2) yes C9 H9 . . .96(2) no C11 C12 . . 1.375(3) yes C11 C16 . . 1.392(3) yes C12 C13 . . 1.386(3) yes C12 H12 . . .92(2) no C13 C14 . . 1.382(3) yes C13 H13 . . .97(2) no C14 O141 . . 1.367(2) yes C14 C15 . . 1.391(3) yes O141 C17 . . 1.428(2) yes C15 C16 . . 1.368(3) yes C15 H15 . . .96(2) no C16 H16 . . .97(2) no C17 C18 . . 1.497(3) yes C17 H171 . . .99(2) no C17 H172 . . 1.01(2) no C18 H181 . . .96(3) no C18 H182 . . 1.02(3) no C18 H183 . . .95(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 767577