#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205197.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_2205197 loop_ _publ_author_name 'Wei Zhou' 'Weixiao Hu' 'Luping Lv' 'Chunnian Xia' _publ_section_title ; 10-(4-Fluorobenzylidene)anthrone ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o592 _journal_page_last o593 _journal_paper_doi 10.1107/S1600536805002655 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C21 H13 F O' _chemical_formula_moiety 'C21 H13 F O' _chemical_formula_sum 'C21 H13 F O' _chemical_formula_weight 300.31 _chemical_name_systematic ; 10-(4-Fluorobenzylidene)anthrone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 109.79(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.044(6) _cell_length_b 11.398(3) _cell_length_c 13.820(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 12.67 _cell_measurement_theta_min 11.14 _cell_volume 1488.7(11) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf--Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo 1995)' _computing_molecular_graphics 'ORTEP-3 for Windows (Version 1.05; Farrugia, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0115 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3137 _diffrn_reflns_theta_full 25.17 _diffrn_reflns_theta_max 25.17 _diffrn_reflns_theta_min 2.15 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.183 _refine_diff_density_min -0.139 _refine_ls_extinction_coef 0.0058(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 2673 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0333 _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^)+(0.0525P)^2^+0.247P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.1032 _reflns_number_gt 2026 _reflns_number_total 2673 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ac6156.cif _cod_data_source_block I _cod_original_cell_volume 1488.7(10) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2205197 _cod_database_fobs_code 2205197 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' 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol F1 0.46323(12) 1.13505(10) 0.22408(10) 0.0977(4) Uani d . 1 F O1 0.04833(13) 0.33472(9) 0.13091(9) 0.0663(3) Uani d . 1 O C1 -0.21168(17) 0.43485(14) 0.01400(11) 0.0580(4) Uani d . 1 C H1 -0.2023 0.3541 0.0092 0.070 Uiso calc R 1 H C2 -0.33601(18) 0.48835(17) -0.04179(13) 0.0685(5) Uani d . 1 C H2 -0.4111 0.4442 -0.0841 0.082 Uiso calc R 1 H C3 -0.34915(17) 0.60847(17) -0.03479(13) 0.0670(5) Uani d . 1 C H3 -0.4344 0.6447 -0.0711 0.080 Uiso calc R 1 H C4 -0.23743(15) 0.67491(15) 0.02528(11) 0.0569(4) Uani d . 1 C H4 -0.2474 0.7559 0.0278 0.068 Uiso calc R 1 H C5 0.01670(14) 0.69201(12) 0.14295(10) 0.0440(3) Uani d . 1 C C6 0.20273(15) 0.68760(14) 0.31943(10) 0.0522(4) Uani d . 1 C H6 0.1967 0.7688 0.3236 0.063 Uiso calc R 1 H C7 0.29415(16) 0.62594(16) 0.40089(11) 0.0614(4) Uani d . 1 C H7 0.3481 0.6658 0.4598 0.074 Uiso calc R 1 H C8 0.30632(17) 0.50583(16) 0.39572(12) 0.0637(4) Uani d . 1 C H8 0.3696 0.4651 0.4504 0.076 Uiso calc R 1 H C9 0.22484(16) 0.44651(14) 0.30976(12) 0.0555(4) Uani d . 1 C H9 0.2334 0.3655 0.3061 0.067 Uiso calc R 1 H C10 0.03015(15) 0.43892(13) 0.14268(10) 0.0481(3) Uani d . 1 C C11 -0.09878(15) 0.50051(13) 0.07809(10) 0.0469(3) Uani d . 1 C C12 0.12921(14) 0.50705(13) 0.22794(10) 0.0464(3) Uani d . 1 C C13 0.11917(14) 0.62930(12) 0.23078(10) 0.0440(3) Uani d . 1 C C14 -0.10890(14) 0.62261(13) 0.08273(10) 0.0458(3) Uani d . 1 C C15 0.03268(14) 0.80040(13) 0.11125(10) 0.0484(3) Uani d . 1 C H15 -0.0457 0.8274 0.0579 0.058 Uiso calc R 1 H C16 0.14984(15) 0.88502(12) 0.14427(10) 0.0465(3) Uani d . 1 C C17 0.11758(15) 1.00391(13) 0.13936(11) 0.0518(4) Uani d . 1 C H17 0.0232 1.0269 0.1168 0.062 Uiso calc R 1 H C18 0.22135(18) 1.08850(14) 0.16698(12) 0.0610(4) Uani d . 1 C H18 0.1984 1.1677 0.1651 0.073 Uiso calc R 1 H C19 0.35952(18) 1.05237(15) 0.19737(13) 0.0632(4) Uani d . 1 C C20 0.39741(17) 0.93670(15) 0.20095(13) 0.0620(4) Uani d . 1 C H20 0.4921 0.9150 0.2209 0.074 Uiso calc R 1 H C21 0.29226(15) 0.85320(13) 0.17435(11) 0.0528(4) Uani d . 1 C H21 0.3165 0.7743 0.1765 0.063 Uiso calc R 1 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 F1 0.0777(7) 0.0807(8) 0.1135(9) -0.0333(6) 0.0046(6) 0.0053(6) O1 0.0806(8) 0.0472(7) 0.0663(7) 0.0053(5) 0.0185(6) -0.0010(5) C1 0.0670(10) 0.0566(9) 0.0463(8) -0.0126(7) 0.0139(7) -0.0021(7) C2 0.0587(10) 0.0786(12) 0.0557(9) -0.0172(9) 0.0031(8) -0.0046(8) C3 0.0474(9) 0.0798(12) 0.0617(10) 0.0008(8) 0.0025(7) 0.0004(9) C4 0.0495(8) 0.0606(9) 0.0528(8) 0.0037(7) 0.0071(7) -0.0026(7) C5 0.0423(7) 0.0470(8) 0.0399(7) 0.0037(6) 0.0105(6) -0.0024(6) C6 0.0518(8) 0.0559(8) 0.0447(8) 0.0007(7) 0.0109(6) -0.0008(6) C7 0.0534(9) 0.0759(11) 0.0451(8) -0.0039(8) 0.0040(7) 0.0004(7) C8 0.0509(8) 0.0739(11) 0.0551(9) 0.0044(8) 0.0034(7) 0.0170(8) C9 0.0501(8) 0.0546(9) 0.0588(9) 0.0063(7) 0.0145(7) 0.0112(7) C10 0.0552(8) 0.0460(8) 0.0457(8) 0.0006(6) 0.0204(7) 0.0023(6) C11 0.0510(8) 0.0504(8) 0.0393(7) -0.0046(6) 0.0151(6) -0.0001(6) C12 0.0431(7) 0.0522(8) 0.0446(7) 0.0045(6) 0.0159(6) 0.0057(6) C13 0.0408(7) 0.0497(8) 0.0414(7) 0.0017(6) 0.0137(6) 0.0012(6) C14 0.0446(7) 0.0523(8) 0.0385(7) -0.0008(6) 0.0114(6) -0.0008(6) C15 0.0442(7) 0.0486(8) 0.0458(7) 0.0051(6) 0.0067(6) 0.0011(6) C16 0.0477(7) 0.0465(8) 0.0412(7) 0.0025(6) 0.0098(6) 0.0029(6) C17 0.0495(8) 0.0508(8) 0.0516(8) 0.0067(7) 0.0123(6) 0.0064(6) C18 0.0706(11) 0.0441(8) 0.0630(10) -0.0007(7) 0.0157(8) 0.0045(7) C19 0.0600(10) 0.0592(10) 0.0601(9) -0.0148(8) 0.0068(7) 0.0045(8) C20 0.0448(8) 0.0708(11) 0.0631(10) 0.0003(7) 0.0088(7) 0.0092(8) C21 0.0501(8) 0.0490(8) 0.0552(8) 0.0067(7) 0.0124(7) 0.0046(6) 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_publ_flag C2 C1 C11 120.56(16) ? C2 C1 H1 119.7 ? C11 C1 H1 119.7 ? C1 C2 C3 119.50(15) ? C1 C2 H2 120.2 ? C3 C2 H2 120.2 ? C4 C3 C2 120.67(16) ? C4 C3 H3 119.7 ? C2 C3 H3 119.7 ? C3 C4 C14 121.03(16) ? C3 C4 H4 119.5 ? C14 C4 H4 119.5 ? C15 C5 C13 125.88(13) yes C15 C5 C14 118.82(12) yes C13 C5 C14 115.17(12) ? C7 C6 C13 120.63(15) ? C7 C6 H6 119.7 ? C13 C6 H6 119.7 ? C8 C7 C6 120.64(15) ? C8 C7 H7 119.7 ? C6 C7 H7 119.7 ? C9 C8 C7 119.82(15) ? C9 C8 H8 120.1 ? C7 C8 H8 120.1 ? C8 C9 C12 120.27(15) ? C8 C9 H9 119.9 ? C12 C9 H9 119.9 ? O1 C10 C11 121.44(14) yes O1 C10 C12 121.76(14) yes C11 C10 C12 116.57(13) ? C1 C11 C14 120.42(14) ? C1 C11 C10 119.07(14) ? C14 C11 C10 120.50(13) ? C9 C12 C13 120.47(14) ? C9 C12 C10 118.65(13) ? C13 C12 C10 120.66(13) ? C6 C13 C12 118.10(13) ? C6 C13 C5 122.23(13) ? C12 C13 C5 119.61(12) ? C11 C14 C4 117.73(13) ? C11 C14 C5 119.69(13) ? C4 C14 C5 122.51(14) ? C5 C15 C16 132.55(13) ? C5 C15 H15 113.7 ? C16 C15 H15 113.7 ? C17 C16 C21 117.81(14) ? C17 C16 C15 118.41(13) yes C21 C16 C15 123.65(13) yes C18 C17 C16 121.85(14) ? C18 C17 H17 119.1 ? C16 C17 H17 119.1 ? C19 C18 C17 117.91(15) ? C19 C18 H18 121.0 ? C17 C18 H18 121.0 ? F1 C19 C20 118.67(16) ? F1 C19 C18 118.57(16) ? C20 C19 C18 122.76(15) ? C19 C20 C21 118.54(15) ? C19 C20 H20 120.7 ? C21 C20 H20 120.7 ? C20 C21 C16 121.09(15) ? C20 C21 H21 119.5 ? C16 C21 H21 119.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag F1 C19 1.3598(19) yes O1 C10 1.2209(17) yes C1 C2 1.369(2) ? C1 C11 1.397(2) ? C1 H1 0.9300 ? C2 C3 1.382(3) ? C2 H2 0.9300 ? C3 C4 1.375(2) ? C3 H3 0.9300 ? C4 C14 1.399(2) ? C4 H4 0.9300 ? C5 C15 1.338(2) yes C5 C13 1.4824(19) ? C5 C14 1.483(2) ? C6 C7 1.380(2) ? C6 C13 1.397(2) ? C6 H6 0.9300 ? C7 C8 1.378(2) ? C7 H7 0.9300 ? C8 C9 1.371(2) ? C8 H8 0.9300 ? C9 C12 1.394(2) ? C9 H9 0.9300 ? C10 C11 1.478(2) ? C10 C12 1.479(2) ? C11 C14 1.398(2) ? C12 C13 1.399(2) ? C15 C16 1.470(2) yes C15 H15 0.9300 ? C16 C17 1.390(2) ? C16 C21 1.396(2) ? C17 C18 1.376(2) ? C17 H17 0.9300 ? C18 C19 1.370(3) ? C18 H18 0.9300 ? C19 C20 1.368(2) ? C20 C21 1.376(2) ? C20 H20 0.9300 ? C21 H21 0.9300 ? 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_publ_flag C11 C1 C2 C3 0.3(3) ? C1 C2 C3 C4 1.9(3) ? C2 C3 C4 C14 -1.6(3) ? C13 C6 C7 C8 1.0(2) ? C6 C7 C8 C9 -1.4(3) ? C7 C8 C9 C12 -0.4(2) ? C2 C1 C11 C14 -2.9(2) ? C2 C1 C11 C10 175.75(14) ? O1 C10 C11 C1 10.5(2) ? C12 C10 C11 C1 -164.17(13) ? O1 C10 C11 C14 -170.94(13) ? C12 C10 C11 C14 14.44(19) ? C8 C9 C12 C13 2.5(2) ? C8 C9 C12 C10 -172.10(14) ? O1 C10 C12 C9 -15.5(2) ? C11 C10 C12 C9 159.09(13) ? O1 C10 C12 C13 169.87(13) ? C11 C10 C12 C13 -15.52(19) ? C7 C6 C13 C12 1.1(2) ? C7 C6 C13 C5 178.16(13) ? C9 C12 C13 C6 -2.8(2) ? C10 C12 C13 C6 171.68(13) ? C9 C12 C13 C5 -179.97(13) ? C10 C12 C13 C5 -5.46(19) ? C15 C5 C13 C6 34.1(2) ? C14 C5 C13 C6 -150.10(13) ? C15 C5 C13 C12 -148.89(14) ? C14 C5 C13 C12 26.92(18) ? C1 C11 C14 C4 3.1(2) ? C10 C11 C14 C4 -175.50(13) ? C1 C11 C14 C5 -173.86(13) ? C10 C11 C14 C5 7.55(19) ? C3 C4 C14 C11 -0.9(2) ? C3 C4 C14 C5 175.94(14) ? C15 C5 C14 C11 148.10(14) ? C13 C5 C14 C11 -28.02(18) ? C15 C5 C14 C4 -28.7(2) ? C13 C5 C14 C4 155.18(13) ? C13 C5 C15 C16 4.4(2) yes C14 C5 C15 C16 -171.30(14) yes C5 C15 C16 C17 -146.85(16) yes C5 C15 C16 C21 37.3(2) yes C21 C16 C17 C18 -2.6(2) ? C15 C16 C17 C18 -178.71(14) ? C16 C17 C18 C19 1.7(2) ? C17 C18 C19 F1 179.46(14) ? C17 C18 C19 C20 0.1(3) ? F1 C19 C20 C21 179.70(14) ? C18 C19 C20 C21 -1.0(3) ? C19 C20 C21 C16 0.0(2) ? C17 C16 C21 C20 1.7(2) ? C15 C16 C21 C20 177.59(14) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21129902 2 PubChem 23829022