#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/60/2006047.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_2006047 loop_ _publ_author_name 'Kawai, Y.' 'Kunitomo, J.' 'Ohno, A.' _publ_contact_author ; Dr. Yasushi Kawai Institute for Chemical Research Kyoto University Uji, Kyoto 611 Japan ; _publ_section_title ; A Novel Function of an Atropisomeric Flavin Model as a Host Compound ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 513 _journal_page_last 515 _journal_paper_doi 10.1107/S0108270197000255 _journal_volume 53 _journal_year 1997 _chemical_formula_analytical 'C69.77 H5.34 N8.45' _chemical_formula_moiety 'C28 H23 N3 O4, C H4 O' _chemical_formula_sum 'C29 H27 N3 O5' _chemical_formula_weight 497.55 _chemical_name_systematic ; 2-[2,4-(3H,10H)-dioxo-10-(4-tert-butylphenyl)pyrimido[4,5-b]quinolin-3-yl]- benzoic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method 'from TEXRAY.INF file' _cell_angle_alpha 90 _cell_angle_beta 103.561(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.613(1) _cell_length_b 21.448(3) _cell_length_c 9.1157(8) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 40.0 _cell_measurement_theta_min 37.2 _cell_volume 2587.3(5) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _computing_data_reduction 'PROCESS TEXSAN (Molecular Structure Corporation, 1993)' _computing_publication_material 'FINISH TEXSAN' _computing_structure_refinement 'LS TEXSAN' _computing_structure_solution 'SAPI91 (Fan, 1991)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator 'Ni filter' _diffrn_radiation_source 'Rigaku rotating Cu anode' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.033 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4169 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 60.0 _diffrn_reflns_theta_min 2.1 _diffrn_standards_decay_% -5.91 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_type '\y scans (North,Phillips & Mathews,1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_meas 1.28 _exptl_crystal_density_method ; flotation in C~6~H~14~/CCl~4~ ; _exptl_crystal_description prismatic _exptl_crystal_F_000 1048 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.259 _refine_diff_density_min -0.189 _refine_ls_extinction_coef 19.872 _refine_ls_extinction_method ; Zachariasen (1967) type 2 Gaussian isotropic ; _refine_ls_goodness_of_fit_all 1.389 _refine_ls_goodness_of_fit_obs 1.786 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 443 _refine_ls_number_reflns 3125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_obs 0.0414 _refine_ls_shift/esd_max 0.0240 _refine_ls_shift/esd_mean 0.0000 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all 0.0817 _refine_ls_wR_factor_obs 0.0682 _reflns_number_observed 3125 _reflns_number_total 3990 _reflns_observed_criterion >3.0sigma(I) _cod_data_source_file de1045.cif _cod_data_source_block CbdFl _cod_original_cell_volume 2587.4(5) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2006047 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -z' 1/2+x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 O1 0.0933(8) -0.0031(6) 0.0539(6) 0.0553(7) -0.0096(6) 0.0818(8) O2 0.0822(7) -0.0119(6) 0.0547(6) 0.0593(7) -0.0087(6) 0.0845(7) O3 0.0695(8) -0.0238(8) 0.0210(6) 0.111(1) 0.0021(8) 0.0665(8) O4 0.105(1) -0.0248(9) 0.0254(7) 0.102(1) 0.0082(8) 0.0598(8) O5 0.0867(9) 0.0044(8) 0.0345(6) 0.091(1) -0.0078(7) 0.0635(7) N1 0.0659(8) 0.0007(7) 0.0328(6) 0.0507(8) -0.0004(7) 0.0592(8) N2 0.0627(8) -0.0017(6) 0.0289(6) 0.0481(8) -0.0023(6) 0.0580(8) N3 0.0560(7) -0.0024(6) 0.0264(6) 0.0505(8) -0.0004(6) 0.0534(7) C1 0.0613(9) 0.0014(8) 0.0270(7) 0.0533(10) 0.0000(8) 0.0555(9) C2 0.0572(9) 0.0007(7) 0.0263(7) 0.0510(9) -0.0005(8) 0.0572(9) C3 0.0532(9) 0.0014(7) 0.0229(7) 0.0492(9) 0.0013(7) 0.0539(9) C4 0.0641(10) 0.0002(8) 0.0325(8) 0.0554(10) -0.0005(8) 0.0603(9) C5 0.0547(9) 0.0001(8) 0.0231(7) 0.0529(10) -0.0004(8) 0.0567(9) C6 0.074(1) -0.0011(9) 0.0362(8) 0.056(1) -0.0042(9) 0.068(1) C7 0.079(1) -0.0041(9) 0.0346(9) 0.055(1) -0.0125(9) 0.078(1) C8 0.076(1) -0.0116(9) 0.0295(9) 0.055(1) -0.0071(9) 0.077(1) C9 0.065(1) -0.0089(8) 0.0297(8) 0.059(1) 0.0006(9) 0.065(1) C10 0.0518(9) 0.0010(7) 0.0179(7) 0.0517(9) 0.0010(7) 0.0521(9) C11 0.0531(9) 0.0018(7) 0.0204(7) 0.0493(9) 0.0026(7) 0.0496(8) C12 0.0562(9) -0.0006(7) 0.0305(7) 0.0468(9) -0.0028(8) 0.0654(10) C13 0.0560(9) 0.0020(8) 0.0292(7) 0.0519(10) -0.0014(8) 0.0654(10) C14 0.075(1) 0.0040(9) 0.0390(9) 0.055(1) 0.0041(9) 0.079(1) C15 0.075(1) -0.0098(9) 0.042(1) 0.053(1) -0.008(1) 0.101(1) C16 0.066(1) -0.0097(10) 0.0265(10) 0.067(1) -0.018(1) 0.092(1) C17 0.0574(10) -0.0011(9) 0.0183(8) 0.063(1) -0.0068(9) 0.068(1) C18 0.066(1) 0.0027(9) 0.0266(8) 0.066(1) 0.0047(9) 0.0598(10) C19 0.0523(8) -0.0017(7) 0.0235(7) 0.0478(9) 0.0023(7) 0.0520(8) C20 0.0569(10) 0.0026(9) 0.0182(7) 0.068(1) 0.0064(8) 0.0497(9) C21 0.0479(9) 0.0012(8) 0.0206(7) 0.072(1) 0.0041(9) 0.0601(10) C22 0.0567(9) -0.0016(8) 0.0240(7) 0.058(1) 0.0014(8) 0.0563(9) C23 0.060(1) 0.0052(10) 0.0187(8) 0.086(1) 0.0111(9) 0.0520(10) C24 0.0480(9) 0.0047(8) 0.0193(7) 0.074(1) 0.0087(9) 0.0595(10) C25 0.071(1) -0.005(1) 0.0359(8) 0.087(1) 0.0053(10) 0.063(1) C26 0.131(2) -0.047(2) 0.076(1) 0.195(3) -0.042(2) 0.096(2) C27 0.077(1) -0.002(1) 0.054(1) 0.126(2) 0.015(2) 0.111(2) C28 0.113(2) 0.009(2) 0.064(1) 0.121(2) 0.051(2) 0.117(2) C29 0.139(2) -0.013(2) 0.045(2) 0.089(2) -0.009(1) 0.089(2) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 1.00 0.6756(1) 0.86064(6) 0.0220(1) 0.0713(4) Uani d . O2 1.00 0.50278(10) 0.93076(6) 0.3564(1) 0.0695(4) Uani d . O3 1.00 0.7332(1) 0.85806(8) 0.4366(2) 0.0814(5) Uani d . O4 1.00 0.6562(1) 0.81049(8) 0.5941(2) 0.0879(5) Uani d . O5 1.00 0.7758(1) 0.87415(7) -0.1961(2) 0.0776(4) Uani d . N1 1.00 0.6930(1) 0.96333(7) 0.0790(2) 0.0556(4) Uani d . N2 1.00 0.5861(1) 0.89587(6) 0.1837(2) 0.0538(4) Uani d . N3 1.00 0.7134(1) 1.06632(6) 0.1542(2) 0.0510(4) Uani d . C1 1.00 0.6542(1) 0.90571(8) 0.0911(2) 0.0545(5) Uani d . C2 1.00 0.5599(1) 0.94143(8) 0.2749(2) 0.0530(5) Uani d . C3 1.00 0.6057(1) 1.00238(8) 0.2646(2) 0.0504(4) Uani d . C4 1.00 0.5871(1) 1.05081(9) 0.3489(2) 0.0570(5) Uani d . C5 1.00 0.6325(1) 1.10953(8) 0.3415(2) 0.0531(5) Uani d . C6 1.00 0.6164(2) 1.16027(9) 0.4305(2) 0.0628(5) Uani d . C7 1.00 0.6627(2) 1.21599(9) 0.4206(2) 0.0677(6) Uani d . C8 1.00 0.7247(2) 1.22309(9) 0.3205(2) 0.0673(6) Uani d . C9 1.00 0.7420(1) 1.17469(9) 0.2318(2) 0.0606(5) Uani d . C10 1.00 0.6964(1) 1.11672(8) 0.2409(2) 0.0509(4) Uani d . C11 1.00 0.6709(1) 1.00860(8) 0.1635(2) 0.0493(4) Uani d . C12 1.00 0.5505(1) 0.83288(8) 0.2005(2) 0.0535(5) Uani d . C13 1.00 0.5833(1) 0.80141(8) 0.3366(2) 0.0553(5) Uani d . C14 1.00 0.5385(2) 0.74437(9) 0.3538(2) 0.0663(5) Uani d . C15 1.00 0.4664(2) 0.71893(9) 0.2397(3) 0.0728(6) Uani d . C16 1.00 0.4362(2) 0.7503(1) 0.1038(3) 0.0735(6) Uani d . C17 1.00 0.4787(1) 0.80758(9) 0.0845(2) 0.0624(5) Uani d . C18 1.00 0.6650(1) 0.82667(9) 0.4591(2) 0.0621(5) Uani d . C19 1.00 0.7759(1) 1.07515(8) 0.0465(2) 0.0488(4) Uani d . C20 1.00 0.8785(1) 1.07006(9) 0.0901(2) 0.0573(5) Uani d . C21 1.00 0.9369(1) 1.08189(9) -0.0127(2) 0.0587(5) Uani d . C22 1.00 0.8934(1) 1.09977(9) -0.1599(2) 0.0553(5) Uani d . C23 1.00 0.7894(1) 1.1035(1) -0.2000(2) 0.0650(6) Uani d . C24 1.00 0.7299(1) 1.09153(10) -0.1000(2) 0.0594(5) Uani d . C25 1.00 0.9560(2) 1.1156(1) -0.2745(2) 0.0703(6) Uani d . C26 1.00 0.9245(3) 1.0735(2) -0.4101(3) 0.132(1) Uani d . C27 1.00 1.0688(2) 1.1101(2) -0.2080(3) 0.0997(9) Uani d . C28 1.00 0.9331(2) 1.1845(2) -0.3217(3) 0.1111(9) Uani d . C29 1.00 0.7798(3) 0.9369(1) -0.2422(3) 0.1023(9) Uani d . H1 1.00 0.542(1) 1.0463(8) 0.418(2) 0.060(5) Uiso calc C4 H2 1.00 0.571(1) 1.1556(8) 0.497(2) 0.062(5) Uiso calc C6 H3 1.00 0.652(1) 1.2497(9) 0.478(2) 0.064(5) Uiso calc C7 H4 1.00 0.759(1) 1.2653(10) 0.309(2) 0.073(6) Uiso calc C8 H5 1.00 0.790(1) 1.1821(8) 0.176(2) 0.063(5) Uiso calc C9 H6 1.00 0.562(1) 0.7222(9) 0.449(2) 0.072(6) Uiso calc C14 H7 1.00 0.429(2) 0.678(1) 0.248(2) 0.090(7) Uiso calc C15 H8 1.00 0.382(2) 0.735(1) 0.015(3) 0.102(8) Uiso calc C16 H9 1.00 0.465(2) 0.8341(10) -0.012(2) 0.078(6) Uiso calc C17 H10 1.00 0.709(2) 0.838(1) 0.688(3) 0.14(1) Uiso calc O4 H11 1.00 0.907(2) 1.0577(10) 0.189(2) 0.071(6) Uiso calc C20 H12 1.00 1.006(2) 1.0764(9) 0.015(2) 0.070(6) Uiso calc C21 H13 1.00 0.759(2) 1.114(1) -0.305(3) 0.094(7) Uiso calc C23 H14 1.00 0.663(1) 1.0988(8) -0.126(2) 0.056(5) Uiso calc C24 H15 1.00 0.850(3) 1.067(2) -0.449(3) 0.14(1) Uiso calc C26 H16 1.00 0.964(2) 1.084(2) -0.471(3) 0.14(1) Uiso calc C26 H17 1.00 0.930(2) 1.019(2) -0.375(3) 0.14(1) Uiso calc C26 H18 1.00 1.089(2) 1.060(2) -0.185(3) 0.13(1) Uiso calc C27 H19 1.00 1.092(3) 1.143(2) -0.117(4) 0.15(1) Uiso calc C27 H20 1.00 1.109(2) 1.120(1) -0.291(3) 0.112(8) Uiso calc C27 H21 1.00 0.859(3) 1.191(2) -0.371(4) 0.15(1) Uiso calc C28 H22 1.00 0.958(3) 1.221(2) -0.212(4) 0.18(1) Uiso calc C28 H23 1.00 0.962(3) 1.192(2) -0.407(4) 0.20(1) Uiso calc C28 H24 1.00 0.708(2) 0.948(1) -0.276(3) 0.112(9) Uiso calc C29 H25 1.00 0.817(2) 0.968(1) -0.158(3) 0.126(10) Uiso calc C29 H26 1.00 0.809(2) 0.941(1) -0.330(3) 0.114(9) Uiso calc C29 H27 1.00 0.745(2) 0.869(1) -0.112(2) 0.088(7) Uiso calc O5 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.018 0.009 'International Tables Vol. IV Table 2.2A' H 0.000 0.000 'International Tables Vol. IV Table 2.2A' N 0.031 0.018 'International Tables Vol. IV Table 2.2A' O 0.049 0.032 'International Tables Vol. IV Table 2.2A' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 2 3 1 0 3 -1 0 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 C1 N1 C11 118.40(10) yes C1 N2 C2 123.60(10) yes C1 N2 C12 119.00(10) yes C2 N2 C12 117.00(10) yes C10 N3 C11 122.40(10) yes C10 N3 C19 119.00(10) yes C11 N3 C19 118.60(10) yes O1 C1 N1 122.1(2) yes O1 C1 N2 117.3(2) yes N1 C1 N2 120.6(2) yes O2 C2 N2 121.8(2) yes O2 C2 C3 123.4(2) yes N2 C2 C3 114.80(10) yes C2 C3 C4 120.8(2) yes C2 C3 C11 117.70(10) yes C4 C3 C11 121.5(2) yes C3 C4 C5 121.1(2) yes C4 C5 C6 122.3(2) yes C4 C5 C10 118.2(2) yes C6 C5 C10 119.6(2) yes C5 C6 C7 120.3(2) yes C6 C7 C8 120.0(2) yes C7 C8 C9 121.3(2) yes C8 C9 C10 119.9(2) yes N3 C10 C5 119.60(10) yes N3 C10 C9 121.4(2) yes C5 C10 C9 119.0(2) yes N1 C11 N3 118.00(10) yes N1 C11 C3 124.8(2) yes N3 C11 C3 117.20(10) yes N2 C12 C13 119.9(2) ? N2 C12 C17 118.7(2) ? C13 C12 C17 121.2(2) ? C12 C13 C14 118.0(2) ? C12 C13 C18 121.5(2) ? C14 C13 C18 120.5(2) ? C13 C14 C15 121.4(2) ? C14 C15 C16 119.8(2) ? C15 C16 C17 120.0(2) ? C12 C17 C16 119.7(2) ? O3 C18 O4 123.5(2) yes O3 C18 C13 123.3(2) yes O4 C18 C13 113.2(2) yes N3 C19 C20 120.90(10) ? N3 C19 C24 118.70(10) ? C20 C19 C24 120.3(2) ? C19 C20 C21 119.9(2) ? C20 C21 C22 121.5(2) ? C21 C22 C23 116.8(2) ? C21 C22 C25 122.8(2) ? C23 C22 C25 120.4(2) ? C22 C23 C24 122.7(2) ? C19 C24 C23 118.9(2) ? C22 C25 C26 109.3(2) ? C22 C25 C27 112.5(2) ? C22 C25 C28 107.0(2) ? C26 C25 C27 110.3(2) ? C26 C25 C28 110.1(2) ? C27 C25 C28 107.6(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.226(2) yes O2 . C2 . 1.217(2) yes O3 . C18 . 1.203(2) yes O4 . C18 . 1.311(2) yes O4 . H10 . 1.14(3) ? O5 . C29 . 1.416(3) yes O5 . H27 . 0.96(2) ? N1 . C1 . 1.359(2) yes N1 . C11 . 1.317(2) yes N2 . C1 . 1.408(2) yes N2 . C2 . 1.383(2) yes N2 . C12 . 1.456(2) yes N3 . C10 . 1.390(2) yes N3 . C11 . 1.378(2) yes N3 . C19 . 1.454(2) yes C2 . C3 . 1.461(2) yes C3 . C4 . 1.351(3) yes C3 . C11 . 1.428(2) yes C4 . C5 . 1.411(3) yes C4 . H1 . 0.99(2) ? C5 . C6 . 1.405(3) yes C5 . C10 . 1.413(2) yes C6 . C7 . 1.364(3) yes C6 . H2 . 0.96(2) ? C7 . C8 . 1.390(3) yes C7 . H3 . 0.92(2) ? C8 . C9 . 1.370(3) yes C8 . H4 . 1.03(2) ? C9 . C10 . 1.400(3) ? C9 . H5 . 0.94(2) ? C12 . C13 . 1.391(3) ? C12 . C17 . 1.372(3) ? C13 . C14 . 1.392(3) ? C13 . C18 . 1.481(3) ? C14 . C15 . 1.366(3) ? C14 . H6 . 0.98(2) ? C15 . C16 . 1.384(3) ? C15 . H7 . 1.03(2) ? C16 . C17 . 1.387(3) ? C16 . H8 . 1.01(2) ? C17 . H9 . 1.03(2) ? C19 . C20 . 1.364(2) ? C19 . C24 . 1.381(2) ? C20 . C21 . 1.387(3) ? C20 . H11 . 0.93(2) ? C21 . C22 . 1.388(3) ? C21 . H12 . 0.92(2) ? C22 . C23 . 1.379(3) ? C22 . C25 . 1.532(3) ? C23 . C24 . 1.379(3) ? C23 . H13 . 0.97(2) ? C24 . H14 . 0.90(2) ? C25 . C26 . 1.510(4) ? C25 . C27 . 1.518(3) ? C25 . C28 . 1.551(4) ? C26 . H15 . 1.00(3) ? C26 . H16 . 0.89(3) ? C26 . H17 . 1.22(3) ? C27 . H18 . 1.11(3) ? C27 . H19 . 1.08(3) ? C27 . H20 . 1.05(3) ? C28 . H21 . 1.02(3) ? C28 . H22 . 1.25(4) ? C28 . H23 . 0.96(4) ? C29 . H24 . 0.98(3) ? C29 . H25 . 1.05(3) ? C29 . H26 . 0.98(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21137796 2 PubChem 139055450