#------------------------------------------------------------------------------ #$Date: 2021-03-23 07:39:36 +0200 (Tue, 23 Mar 2021) $ #$Revision: 263236 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242503.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7242503 loop_ _publ_author_name 'Chang, Meng-Yang' 'Tsai, Min-Chen' 'Lin, Chun-Yi' _publ_section_title ; A novel one-pot synthesis of flavones ; _journal_issue 19 _journal_name_full 'RSC Advances' _journal_page_first 11655 _journal_page_last 11662 _journal_paper_doi 10.1039/D1RA00534K _journal_volume 11 _journal_year 2021 _chemical_absolute_configuration rm _chemical_formula_sum 'C17 H13 F O4' _chemical_formula_weight 300.27 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yac' _space_group_name_H-M_alt 'P 1 n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2019-10-03 deposited with the CCDC. 2021-03-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.222(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.0051(3) _cell_length_b 10.1298(8) _cell_length_c 16.3327(12) _cell_measurement_reflns_used 3887 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.3172 _cell_measurement_theta_min 2.3664 _cell_volume 662.13(9) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_unetI/netI 0.0297 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 3830 _diffrn_reflns_point_group_measured_fraction_full 0.756 _diffrn_reflns_point_group_measured_fraction_max 0.738 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.380 _diffrn_reflns_theta_min 2.010 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6849 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/4 (Bruker AXS Inc.)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description lamelar _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.207 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 594 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.3(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 1987 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.118 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0288 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.1217P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.0827 _reflns_Friedel_coverage 0.483 _reflns_Friedel_fraction_full 0.517 _reflns_Friedel_fraction_max 0.483 _reflns_number_gt 1898 _reflns_number_total 1987 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra00534k2.cif _cod_data_source_block 190902LT_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P n' _cod_database_code 7242503 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2014/6 _shelx_res_file ; TITL 190902LT_0m in Pn CELL 0.71073 4.0051 10.1298 16.3327 90.000 92.222 90.000 ZERR 2.00 0.0003 0.0008 0.0012 0.000 0.003 0.000 LATT -1 SYMM x+1/2, -y, z+1/2 SFAC C H O F UNIT 34 26 8 2 TEMP -173.000 ACTA L.S. 4 FMAP 2 PLAN 5 BOND $H WGHT 0.043900 0.121700 FVAR 0.92398 F1 4 1.035990 0.105934 0.372843 11.00000 0.03231 0.02688 = 0.02329 -0.00350 0.00957 -0.00174 O1 3 -0.374068 0.434801 0.951251 11.00000 0.02898 0.01754 = 0.01741 0.00041 0.00670 0.00028 O2 3 0.337305 0.257264 0.637084 11.00000 0.02131 0.01377 = 0.01755 -0.00036 0.00270 0.00226 O3 3 0.555917 -0.134464 0.615614 11.00000 0.04135 0.01266 = 0.02399 -0.00092 0.00376 0.00347 O4 3 -0.255210 0.562581 0.818646 11.00000 0.03699 0.01415 = 0.01834 0.00238 0.00923 0.00500 C1 1 -0.438961 0.368242 1.026260 11.00000 0.03106 0.02359 = 0.01758 0.00387 0.00534 -0.00041 AFIX 137 H1 2 -0.607312 0.299434 1.015863 11.00000 -1.50000 H6 2 -0.521844 0.431803 1.065892 11.00000 -1.50000 H7 2 -0.232168 0.327905 1.048396 11.00000 -1.50000 AFIX 0 C2 1 -0.229790 0.363639 0.891368 11.00000 0.01511 0.01880 = 0.01491 -0.00136 0.00257 -0.00326 C3 1 -0.160216 0.432916 0.819345 11.00000 0.02071 0.01393 = 0.01881 -0.00007 -0.00048 0.00131 C4 1 -0.006186 0.370204 0.756266 11.00000 0.02067 0.01669 = 0.01669 0.00174 -0.00168 -0.00253 AFIX 43 H10 2 0.043387 0.418154 0.708248 11.00000 -1.20000 AFIX 0 C5 1 0.078599 0.235380 0.762348 11.00000 0.01495 0.01501 = 0.01794 -0.00213 -0.00158 -0.00105 C6 1 0.249513 0.170178 0.696016 11.00000 0.01759 0.01629 = 0.01517 0.00218 -0.00326 -0.00256 C7 1 0.512066 0.213772 0.571604 11.00000 0.01244 0.01754 = 0.01506 -0.00213 -0.00001 0.00066 C8 1 0.597878 0.082051 0.562315 11.00000 0.01507 0.01663 = 0.01546 -0.00103 -0.00272 -0.00035 C9 1 0.777112 0.045603 0.494283 11.00000 0.01868 0.01628 = 0.01909 -0.00411 0.00006 0.00100 AFIX 43 H13 2 0.840157 -0.043746 0.486296 11.00000 -1.20000 AFIX 0 C10 1 0.860434 0.140929 0.439268 11.00000 0.01721 0.02388 = 0.01633 -0.00440 0.00257 -0.00264 C11 1 0.320903 0.039393 0.690340 11.00000 0.02386 0.01561 = 0.01366 0.00160 0.00046 -0.00063 AFIX 43 H2 2 0.252572 -0.018028 0.732522 11.00000 -1.20000 AFIX 0 C12 1 0.495333 -0.015393 0.623189 11.00000 0.02114 0.01537 = 0.01611 -0.00042 -0.00171 -0.00029 C13 1 -0.181399 0.638518 0.747579 11.00000 0.04936 0.01830 = 0.02747 0.00524 0.01495 0.01194 AFIX 137 H3 2 0.060436 0.638752 0.740459 11.00000 -1.50000 H5 2 -0.259621 0.729351 0.754526 11.00000 -1.50000 H4 2 -0.294527 0.599389 0.699144 11.00000 -1.50000 AFIX 0 C14 1 -0.149788 0.230577 0.897209 11.00000 0.02154 0.01792 = 0.01794 0.00297 0.00040 -0.00267 AFIX 43 H8 2 -0.198169 0.182606 0.945303 11.00000 -1.20000 AFIX 0 C15 1 0.001105 0.167441 0.832726 11.00000 0.02031 0.01409 = 0.02320 0.00081 -0.00054 -0.00092 AFIX 43 H9 2 0.051995 0.076044 0.837006 11.00000 -1.20000 AFIX 0 C16 1 0.596698 0.308773 0.514747 11.00000 0.01973 0.01554 = 0.02222 0.00065 -0.00125 -0.00108 AFIX 43 H12 2 0.533105 0.398200 0.522149 11.00000 -1.20000 AFIX 0 C17 1 0.773305 0.272782 0.447546 11.00000 0.01949 0.02114 = 0.01900 0.00203 0.00006 -0.00302 AFIX 43 H11 2 0.833732 0.336359 0.408006 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 190902LT_0m in Pn REM R1 = 0.0288 for 1898 Fo > 4sig(Fo) and 0.0307 for all 1987 data REM 201 parameters refined using 2 restraints END WGHT 0.0438 0.1222 REM Highest difference peak 0.207, deepest hole -0.209, 1-sigma level 0.045 Q1 1 0.4889 0.1404 0.5615 11.00000 0.05 0.21 Q2 1 0.6031 0.1456 0.5812 11.00000 0.05 0.19 Q3 1 0.4942 0.0351 0.5843 11.00000 0.05 0.18 Q4 1 0.1465 0.1067 0.6933 11.00000 0.05 0.17 Q5 1 0.2422 -0.2399 0.6604 11.00000 0.05 0.17 ; _shelx_res_checksum 13921 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y, z+1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 1.0360(4) 0.10593(16) 0.37284(10) 0.0273(4) Uani 1 1 d . . . . . O1 O -0.3741(5) 0.43480(17) 0.95125(12) 0.0212(4) Uani 1 1 d . . . . . O2 O 0.3373(4) 0.25726(17) 0.63708(10) 0.0175(4) Uani 1 1 d . . . . . O3 O 0.5559(5) -0.13446(17) 0.61561(13) 0.0259(5) Uani 1 1 d . . . . . O4 O -0.2552(5) 0.56258(18) 0.81865(12) 0.0229(4) Uani 1 1 d . . . . . C1 C -0.4390(8) 0.3682(3) 1.02626(17) 0.0240(6) Uani 1 1 d . . . . . H1 H -0.6073 0.2994 1.0159 0.036 Uiso 1 1 calc R U . . . H6 H -0.5218 0.4318 1.0659 0.036 Uiso 1 1 calc R U . . . H7 H -0.2322 0.3279 1.0484 0.036 Uiso 1 1 calc R U . . . C2 C -0.2298(6) 0.3636(2) 0.89137(16) 0.0162(5) Uani 1 1 d . . . . . C3 C -0.1602(6) 0.4329(3) 0.81935(16) 0.0178(6) Uani 1 1 d . . . . . C4 C -0.0062(7) 0.3702(2) 0.75627(16) 0.0181(6) Uani 1 1 d . . . . . H10 H 0.0434 0.4182 0.7082 0.022 Uiso 1 1 calc R U . . . C5 C 0.0786(7) 0.2354(2) 0.76235(16) 0.0160(6) Uani 1 1 d . . . . . C6 C 0.2495(6) 0.1702(3) 0.69602(15) 0.0164(6) Uani 1 1 d . . . . . C7 C 0.5121(6) 0.2138(2) 0.57160(15) 0.0150(6) Uani 1 1 d . . . . . C8 C 0.5979(6) 0.0821(3) 0.56232(16) 0.0158(6) Uani 1 1 d . . . . . C9 C 0.7771(6) 0.0456(3) 0.49428(16) 0.0180(6) Uani 1 1 d . . . . . H13 H 0.8402 -0.0437 0.4863 0.022 Uiso 1 1 calc R U . . . C10 C 0.8604(6) 0.1409(3) 0.43927(16) 0.0191(6) Uani 1 1 d . . . . . C11 C 0.3209(7) 0.0394(3) 0.69034(16) 0.0177(6) Uani 1 1 d . . . . . H2 H 0.2526 -0.0180 0.7325 0.021 Uiso 1 1 calc R U . . . C12 C 0.4953(6) -0.0154(2) 0.62319(16) 0.0176(6) Uani 1 1 d . . . . . C13 C -0.1814(9) 0.6385(3) 0.7476(2) 0.0314(7) Uani 1 1 d . . . . . H3 H 0.0604 0.6388 0.7405 0.047 Uiso 1 1 calc R U . . . H5 H -0.2596 0.7294 0.7545 0.047 Uiso 1 1 calc R U . . . H4 H -0.2945 0.5994 0.6991 0.047 Uiso 1 1 calc R U . . . C14 C -0.1498(7) 0.2306(3) 0.89721(16) 0.0191(6) Uani 1 1 d . . . . . H8 H -0.1982 0.1826 0.9453 0.023 Uiso 1 1 calc R U . . . C15 C 0.0011(7) 0.1674(2) 0.83273(16) 0.0192(6) Uani 1 1 d . . . . . H9 H 0.0520 0.0760 0.8370 0.023 Uiso 1 1 calc R U . . . C16 C 0.5967(7) 0.3088(3) 0.51475(16) 0.0192(6) Uani 1 1 d . . . . . H12 H 0.5331 0.3982 0.5221 0.023 Uiso 1 1 calc R U . . . C17 C 0.7733(6) 0.2728(3) 0.44755(17) 0.0199(6) Uani 1 1 d . . . . . H11 H 0.8337 0.3364 0.4080 0.024 Uiso 1 1 calc R U . . . 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 F1 0.0323(10) 0.0269(9) 0.0233(9) -0.0035(7) 0.0096(7) -0.0017(7) O1 0.0290(11) 0.0175(9) 0.0174(9) 0.0004(8) 0.0067(8) 0.0003(8) O2 0.0213(10) 0.0138(9) 0.0176(9) -0.0004(7) 0.0027(8) 0.0023(7) O3 0.0413(12) 0.0127(9) 0.0240(10) -0.0009(8) 0.0038(9) 0.0035(8) O4 0.0370(12) 0.0141(9) 0.0183(10) 0.0024(8) 0.0092(8) 0.0050(8) C1 0.0311(16) 0.0236(14) 0.0176(15) 0.0039(12) 0.0053(12) -0.0004(13) C2 0.0151(14) 0.0188(13) 0.0149(13) -0.0014(11) 0.0026(10) -0.0033(10) C3 0.0207(16) 0.0139(12) 0.0188(14) -0.0001(10) -0.0005(11) 0.0013(10) C4 0.0207(15) 0.0167(12) 0.0167(14) 0.0017(11) -0.0017(11) -0.0025(11) C5 0.0149(13) 0.0150(12) 0.0179(13) -0.0021(10) -0.0016(10) -0.0011(10) C6 0.0176(14) 0.0163(13) 0.0152(14) 0.0022(11) -0.0033(10) -0.0026(11) C7 0.0124(13) 0.0175(12) 0.0151(13) -0.0021(10) 0.0000(10) 0.0007(11) C8 0.0151(14) 0.0166(12) 0.0155(13) -0.0010(10) -0.0027(10) -0.0004(10) C9 0.0187(15) 0.0163(13) 0.0191(14) -0.0041(11) 0.0001(11) 0.0010(10) C10 0.0172(15) 0.0239(14) 0.0163(14) -0.0044(11) 0.0026(11) -0.0026(11) C11 0.0239(16) 0.0156(12) 0.0137(13) 0.0016(11) 0.0005(11) -0.0006(11) C12 0.0211(15) 0.0154(12) 0.0161(14) -0.0004(11) -0.0017(11) -0.0003(11) C13 0.049(2) 0.0183(14) 0.0275(16) 0.0052(12) 0.0150(15) 0.0119(14) C14 0.0215(14) 0.0179(13) 0.0179(13) 0.0030(11) 0.0004(11) -0.0027(11) C15 0.0203(15) 0.0141(12) 0.0232(14) 0.0008(11) -0.0005(11) -0.0009(10) C16 0.0197(15) 0.0155(12) 0.0222(14) 0.0006(11) -0.0013(11) -0.0011(11) C17 0.0195(15) 0.0211(13) 0.0190(14) 0.0020(11) 0.0001(11) -0.0030(11) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 O1 C1 117.5(2) . . ? C6 O2 C7 119.73(19) . . ? C3 O4 C13 117.2(2) . . ? O1 C1 H1 109.5 . . ? O1 C1 H6 109.5 . . ? H1 C1 H6 109.5 . . ? O1 C1 H7 109.5 . . ? H1 C1 H7 109.5 . . ? H6 C1 H7 109.5 . . ? O1 C2 C14 124.6(2) . . ? O1 C2 C3 116.1(2) . . ? C14 C2 C3 119.3(3) . . ? O4 C3 C4 124.7(2) . . ? O4 C3 C2 115.0(2) . . ? C4 C3 C2 120.3(2) . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H10 119.7 . . ? C5 C4 H10 119.7 . . ? C15 C5 C4 118.6(3) . . ? C15 C5 C6 121.1(2) . . ? C4 C5 C6 120.3(2) . . ? C11 C6 O2 121.5(2) . . ? C11 C6 C5 126.6(2) . . ? O2 C6 C5 111.9(2) . . ? O2 C7 C8 122.0(2) . . ? O2 C7 C16 116.3(2) . . ? C8 C7 C16 121.7(2) . . ? C7 C8 C9 118.6(2) . . ? C7 C8 C12 119.6(2) . . ? C9 C8 C12 121.8(2) . . ? C10 C9 C8 118.8(2) . . ? C10 C9 H13 120.6 . . ? C8 C9 H13 120.6 . . ? F1 C10 C9 119.0(2) . . ? F1 C10 C17 117.9(2) . . ? C9 C10 C17 123.1(3) . . ? C6 C11 C12 122.6(2) . . ? C6 C11 H2 118.7 . . ? C12 C11 H2 118.7 . . ? O3 C12 C11 123.8(2) . . ? O3 C12 C8 121.7(2) . . ? C11 C12 C8 114.5(2) . . ? O4 C13 H3 109.5 . . ? O4 C13 H5 109.5 . . ? H3 C13 H5 109.5 . . ? O4 C13 H4 109.5 . . ? H3 C13 H4 109.5 . . ? H5 C13 H4 109.5 . . ? C2 C14 C15 120.0(3) . . ? C2 C14 H8 120.0 . . ? C15 C14 H8 120.0 . . ? C5 C15 C14 121.2(2) . . ? C5 C15 H9 119.4 . . ? C14 C15 H9 119.4 . . ? C17 C16 C7 119.7(2) . . ? C17 C16 H12 120.1 . . ? C7 C16 H12 120.1 . . ? C16 C17 C10 118.1(3) . . ? C16 C17 H11 121.0 . . ? C10 C17 H11 121.0 . . ? 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 F1 C10 1.362(3) . ? O1 C2 1.362(3) . ? O1 C1 1.431(3) . ? O2 C6 1.362(3) . ? O2 C7 1.373(3) . ? O3 C12 1.237(3) . ? O4 C3 1.367(3) . ? O4 C13 1.433(4) . ? C1 H1 0.9800 . ? C1 H6 0.9800 . ? C1 H7 0.9800 . ? C2 C14 1.388(4) . ? C2 C3 1.407(4) . ? C3 C4 1.377(4) . ? C4 C5 1.410(3) . ? C4 H10 0.9500 . ? C5 C15 1.385(4) . ? C5 C6 1.462(4) . ? C6 C11 1.359(3) . ? C7 C8 1.388(3) . ? C7 C16 1.388(4) . ? C8 C9 1.396(4) . ? C8 C12 1.471(4) . ? C9 C10 1.369(4) . ? C9 H13 0.9500 . ? C10 C17 1.388(4) . ? C11 C12 1.435(4) . ? C11 H2 0.9500 . ? C13 H3 0.9800 . ? C13 H5 0.9800 . ? C13 H4 0.9800 . ? C14 C15 1.390(4) . ? C14 H8 0.9500 . ? C15 H9 0.9500 . ? C16 C17 1.378(4) . ? C16 H12 0.9500 . ? C17 H11 0.9500 . ?