#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203249.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_2203249 loop_ _publ_author_name 'Yu, Zhifang' 'Gu, Xiuyan' 'Zhao, Bing' 'Cao, Xiaoqiang' _publ_section_title ; 3-(2,4-Dichlorophenyl)-1-(2-furyl)-3-hydroxypropan-1-one ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o168 _journal_page_last o169 _journal_paper_doi 10.1107/S1600536803029568 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C13 H10 Cl2 O3' _chemical_formula_moiety 'C13 H10 Cl2 O3' _chemical_formula_sum 'C13 H10 Cl2 O3' _chemical_formula_weight 285.11 _chemical_melting_point 340 _chemical_name_systematic ; 3-(2,4-Dichlorophenyl)-1-(2-furyl)-3-hydroxypropan-1-one ; _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_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 79.464(4) _cell_angle_beta 72.596(4) _cell_angle_gamma 79.918(5) _cell_formula_units_Z 2 _cell_length_a 7.933(2) _cell_length_b 8.737(3) _cell_length_c 9.907(3) _cell_measurement_reflns_used 989 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.28 _cell_measurement_theta_min 2.71 _cell_volume 638.9(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997) ' _computing_data_reduction SMART _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\y and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3322 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.18 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.504 _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_correction_T_min 0.882 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 292 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.324 _refine_diff_density_min -0.438 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2246 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.1932P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1018 _refine_ls_wR_factor_ref 0.1109 _reflns_number_gt 1808 _reflns_number_total 2246 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ww6151.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2203249 _cod_database_fobs_code 2203249 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl1 0.43230(8) 0.14544(9) 0.77489(7) 0.0706(3) Uani d . 1 Cl Cl2 -0.17314(9) -0.08303(9) 0.84055(8) 0.0758(3) Uani d . 1 Cl O1 0.3100(2) 0.46997(19) 0.41418(17) 0.0588(4) Uani d . 1 O H1 0.2657 0.5367 0.4675 0.088 Uiso calc R 1 H O2 0.7640(2) 0.3692(2) 0.34604(18) 0.0656(5) Uani d . 1 O O3 0.8364(2) 0.4239(2) 0.05729(18) 0.0687(5) Uani d . 1 O C1 0.0880(3) 0.2283(3) 0.5397(2) 0.0512(6) Uani d . 1 C H1A 0.0737 0.2896 0.4557 0.061 Uiso calc R 1 H C2 -0.0390(3) 0.1325(3) 0.6170(2) 0.0535(6) Uani d . 1 C H2 -0.1371 0.1285 0.5854 0.064 Uiso calc R 1 H C3 -0.0178(3) 0.0426(3) 0.7423(2) 0.0483(5) Uani d . 1 C C4 0.1239(3) 0.0486(3) 0.7919(2) 0.0466(5) Uani d . 1 C H4 0.1356 -0.0109 0.8774 0.056 Uiso calc R 1 H C5 0.2496(3) 0.1456(3) 0.7117(2) 0.0436(5) Uani d . 1 C C6 0.2371(3) 0.2358(2) 0.5837(2) 0.0411(5) Uani d . 1 C C7 0.3811(3) 0.3332(3) 0.4909(2) 0.0460(5) Uani d . 1 C H7 0.4445 0.3635 0.5510 0.055 Uiso calc R 1 H C8 0.5123(3) 0.2362(3) 0.3812(2) 0.0569(6) Uani d . 1 C H8A 0.5584 0.1389 0.4304 0.068 Uiso calc R 1 H H8B 0.4503 0.2100 0.3194 0.068 Uiso calc R 1 H C9 0.6662(3) 0.3234(3) 0.2911(2) 0.0499(5) Uani d . 1 C C10 0.6960(3) 0.3472(3) 0.1375(2) 0.0473(5) Uani d . 1 C C11 0.6134(3) 0.3081(3) 0.0499(3) 0.0561(6) Uani d . 1 C H11 0.5142 0.2548 0.0773 0.067 Uiso calc R 1 H C12 0.7062(4) 0.3635(3) -0.0913(3) 0.0663(7) Uani d . 1 C H12 0.6802 0.3541 -0.1747 0.080 Uiso calc R 1 H C13 0.8379(4) 0.4317(4) -0.0811(3) 0.0732(8) Uani d . 1 C H13 0.9203 0.4788 -0.1586 0.088 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 Cl1 0.0547(4) 0.1037(6) 0.0590(4) -0.0306(3) -0.0275(3) 0.0139(3) Cl2 0.0567(4) 0.0902(5) 0.0782(5) -0.0356(4) -0.0115(3) 0.0075(4) O1 0.0757(12) 0.0515(9) 0.0461(9) -0.0115(8) -0.0158(8) 0.0025(7) O2 0.0646(11) 0.0862(13) 0.0510(10) -0.0243(10) -0.0096(8) -0.0190(9) O3 0.0678(11) 0.0902(13) 0.0469(10) -0.0369(10) -0.0017(8) -0.0050(9) C1 0.0560(13) 0.0611(14) 0.0385(11) -0.0097(11) -0.0174(10) -0.0021(10) C2 0.0459(13) 0.0686(15) 0.0513(13) -0.0121(11) -0.0169(10) -0.0114(11) C3 0.0392(11) 0.0540(13) 0.0493(13) -0.0106(10) -0.0058(10) -0.0077(10) C4 0.0426(12) 0.0525(13) 0.0406(11) -0.0061(10) -0.0090(9) 0.0001(9) C5 0.0381(11) 0.0533(12) 0.0400(11) -0.0065(9) -0.0112(9) -0.0064(9) C6 0.0451(11) 0.0448(11) 0.0330(10) -0.0075(9) -0.0074(9) -0.0083(9) C7 0.0539(13) 0.0489(12) 0.0350(11) -0.0139(10) -0.0086(9) -0.0048(9) C8 0.0634(15) 0.0554(14) 0.0474(13) -0.0200(12) 0.0018(11) -0.0127(11) C9 0.0507(13) 0.0507(13) 0.0460(12) -0.0087(10) -0.0045(10) -0.0137(10) C10 0.0466(12) 0.0481(12) 0.0439(12) -0.0109(10) -0.0046(10) -0.0063(10) C11 0.0556(14) 0.0597(14) 0.0545(14) -0.0095(11) -0.0147(11) -0.0105(11) C12 0.0792(19) 0.0743(18) 0.0461(14) -0.0050(15) -0.0202(13) -0.0096(12) C13 0.084(2) 0.085(2) 0.0413(14) -0.0208(16) -0.0020(13) -0.0025(13) 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 ; Cl Cl 0.1484 0.1585 ; 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 ; 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 C7 O1 H1 109.5 ? C13 O3 C10 106.5(2) yes C2 C1 C6 121.9(2) ? C2 C1 H1A 119.0 ? C6 C1 H1A 119.0 ? C1 C2 C3 118.8(2) ? C1 C2 H2 120.6 ? C3 C2 H2 120.6 ? C4 C3 C2 121.6(2) ? C4 C3 Cl2 118.45(17) ? C2 C3 Cl2 119.98(17) yes C3 C4 C5 118.3(2) ? C3 C4 H4 120.8 ? C5 C4 H4 120.8 ? C6 C5 C4 122.57(19) ? C6 C5 Cl1 120.29(16) yes C4 C5 Cl1 117.11(16) ? C5 C6 C1 116.80(19) ? C5 C6 C7 122.51(19) ? C1 C6 C7 120.63(18) ? O1 C7 C6 111.93(18) yes O1 C7 C8 107.32(18) ? C6 C7 C8 109.40(17) ? O1 C7 H7 109.4 ? C6 C7 H7 109.4 ? C8 C7 H7 109.4 ? C9 C8 C7 111.98(18) ? C9 C8 H8A 109.2 ? C7 C8 H8A 109.2 ? C9 C8 H8B 109.2 ? C7 C8 H8B 109.2 ? H8A C8 H8B 107.9 ? O2 C9 C10 121.3(2) yes O2 C9 C8 121.1(2) ? C10 C9 C8 117.6(2) ? C11 C10 O3 109.1(2) ? C11 C10 C9 133.8(2) ? O3 C10 C9 117.1(2) yes C10 C11 C12 107.1(2) ? C10 C11 H11 126.5 ? C12 C11 H11 126.5 ? C13 C12 C11 106.2(2) ? C13 C12 H12 126.9 ? C11 C12 H12 126.9 ? C12 C13 O3 111.1(2) ? C12 C13 H13 124.4 ? O3 C13 H13 124.4 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C5 1.742(2) yes Cl2 C3 1.743(2) yes O1 C7 1.418(3) yes O1 H1 0.8200 ? O2 C9 1.224(3) yes O3 C13 1.357(3) ? O3 C10 1.363(3) ? C1 C2 1.379(3) ? C1 C6 1.393(3) ? C1 H1A 0.9300 ? C2 C3 1.381(3) ? C2 H2 0.9300 ? C3 C4 1.367(3) ? C4 C5 1.386(3) ? C4 H4 0.9300 ? C5 C6 1.386(3) ? C6 C7 1.516(3) ? C7 C8 1.528(3) ? C7 H7 0.9800 ? C8 C9 1.514(3) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 C10 1.449(3) ? C10 C11 1.352(3) ? C11 C12 1.412(4) ? C11 H11 0.9300 ? C12 C13 1.326(4) ? C12 H12 0.9300 ? C13 H13 0.9300 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 O2 2_666 0.82 2.09 2.839(3) 152 yes C7 H7 Cl1 . 0.98 2.64 3.088(2) 108 yes C12 H12 O1 2_665 0.93 2.57 3.293(3) 135 yes 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 C6 C1 C2 C3 0.5(4) ? C1 C2 C3 C4 1.1(4) ? C1 C2 C3 Cl2 -178.54(17) ? C2 C3 C4 C5 -1.3(3) ? Cl2 C3 C4 C5 178.37(16) ? C3 C4 C5 C6 -0.1(3) ? C3 C4 C5 Cl1 -177.88(17) ? C4 C5 C6 C1 1.6(3) ? Cl1 C5 C6 C1 179.31(16) ? C4 C5 C6 C7 -175.64(19) ? Cl1 C5 C6 C7 2.0(3) ? C2 C1 C6 C5 -1.8(3) ? C2 C1 C6 C7 175.5(2) ? C5 C6 C7 O1 -149.0(2) yes C1 C6 C7 O1 33.8(3) ? C5 C6 C7 C8 92.2(2) ? C1 C6 C7 C8 -85.0(3) ? O1 C7 C8 C9 62.0(3) yes C6 C7 C8 C9 -176.37(19) ? C7 C8 C9 O2 58.6(3) yes C7 C8 C9 C10 -122.8(2) ? C13 O3 C10 C11 0.3(3) ? C13 O3 C10 C9 179.8(2) ? O2 C9 C10 C11 178.9(3) yes C8 C9 C10 C11 0.3(4) ? O2 C9 C10 O3 -0.5(3) ? C8 C9 C10 O3 -179.1(2) ? O3 C10 C11 C12 -0.2(3) ? C9 C10 C11 C12 -179.7(3) ? C10 C11 C12 C13 0.1(3) ? C11 C12 C13 O3 0.1(3) ? C10 O3 C13 C12 -0.2(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066456