#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008916.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_2008916 loop_ _publ_author_name 'Kakou-Yao, R.' 'Saba, A.' 'Ebby, N.' 'Pierrot, M.' 'Aycard, J. P.' _publ_section_title ; Tautom\'erie de la 4-(hydroxyph\'enylm\'ethyl\`ene) isochroman-1,3 dione \`a l'\'etat solide ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1591 _journal_page_last 1593 _journal_paper_doi 10.1107/S0108270199006782 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C16 H10 O4' _chemical_formula_weight 266.25 _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_type_scat_source 'Waasmaier & Kirfel (1995)' _cell_angle_alpha 90.000 _cell_angle_beta 105.3580(10) _cell_angle_gamma 90.000 _cell_formula_units_Z 4 _cell_length_a 10.1700(10) _cell_length_b 12.8970(10) _cell_length_c 9.8010(10) _cell_measurement_reflns_used 8495 _cell_measurement_temperature 298 _cell_measurement_theta_max 25.6 _cell_measurement_theta_min 1 _cell_volume 1239.6(2) _computing_cell_refinement 'Kappa CCD Reference Manual (Nonius, 1998)' _computing_data_reduction 'MAXUS (Mackay, 1998)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material MAXUS _computing_structure_refinement MAXUS _computing_structure_solution MAXUS _diffrn_measurement_device 'Kappa CCD' _diffrn_measurement_method \f-scan _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 8495 _diffrn_reflns_theta_max 25.61 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type 'not measured' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.42 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.54 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 181 _refine_ls_number_reflns 1865 _refine_ls_R_factor_gt 0.042 _refine_ls_shift/esd_mean 0.001 _refine_ls_shift/su_max 0.005 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'Count statistics' _refine_ls_wR_factor_ref 0.074 _reflns_number_gt 1865 _reflns_number_total 2451 _reflns_observed_criterion I>2\s(I) _cod_data_source_file gs1041.cif _cod_data_source_block block _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 20 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1239.6(3) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2008916 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,-z -x,+y+1/2,-z+1/2 +x,-y+1/2,+z+1/2 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 O2 0.0517(3) 0.0598(4) 0.0579(3) 0.0038(3) -.0022(3) 0.0111(3) O19 0.0689(4) 0.0481(4) 0.0782(4) 0.0131(3) 0.0120(3) 0.0086(3) O20 0.0725(4) 0.0465(4) 0.0794(4) 0.0072(3) 0.0002(3) -.0115(3) O18 0.0636(4) 0.0904(5) 0.0658(4) -.0113(3) -.0188(3) 0.0078(3) C10 0.0368(4) 0.0458(4) 0.0457(4) 0.0009(3) 0.0119(3) -.0003(3) C12 0.0436(4) 0.0408(4) 0.0462(4) -.0045(3) 0.0061(3) -.0053(3) C5 0.0449(4) 0.0470(5) 0.0467(4) 0.0006(3) 0.0058(3) 0.0000(3) C17 0.0593(5) 0.0518(5) 0.0497(5) -.0036(4) 0.0162(4) -.0053(3) C9 0.0367(4) 0.0544(5) 0.0472(4) -.0023(3) 0.0083(3) -.0018(3) C11 0.0518(5) 0.0430(5) 0.0484(5) 0.0014(3) 0.0127(3) -.0034(3) C14 0.0491(5) 0.0584(5) 0.0656(6) 0.0047(4) 0.0107(4) -.0073(4) C15 0.0548(5) 0.0482(5) 0.0602(5) 0.0012(4) -.0055(4) 0.0004(4) C4 0.0416(4) 0.0454(5) 0.0460(4) 0.0032(3) 0.0096(3) 0.0013(3) C13 0.0554(5) 0.0610(5) 0.0418(4) 0.0017(4) 0.0086(3) -.0049(3) C16 0.0737(6) 0.0543(5) 0.0433(4) -.0031(4) 0.0014(4) 0.0017(3) C6 0.0513(5) 0.0472(5) 0.0632(5) 0.0040(4) 0.0121(4) 0.0036(4) C8 0.0442(5) 0.0611(6) 0.0621(5) -.0066(4) 0.0043(4) -.0109(4) C1 0.0415(4) 0.0654(6) 0.0532(5) -.0038(4) 0.0048(4) 0.0048(4) C7 0.0529(5) 0.0472(5) 0.0785(6) -.0043(4) 0.0111(4) -.0093(4) C3 0.0440(4) 0.0527(5) 0.0551(5) 0.0044(4) 0.0128(3) 0.0073(3) loop_ _atom_site_label _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_occupancy O2 0.44609(6) 0.05201(4) 0.66535(6) 0.0594(3) Uani 1.00 O19 0.36510(6) -0.07669(5) 0.52356(7) 0.0676(3) Uani 1.00 O20 0.15300(6) -0.05819(5) 0.32655(7) 0.0699(3) Uani 1.00 O18 0.55125(7) 0.17496(5) 0.80735(7) 0.0783(4) Uani 1.00 C10 0.28446(7) 0.19963(5) 0.48205(7) 0.0437(3) Uani 1.00 C12 0.03068(7) 0.09442(6) 0.27437(8) 0.0452(4) Uani 1.00 C5 0.21998(8) 0.27780(6) 0.38831(8) 0.0480(4) Uani 1.00 C17 0.00121(9) 0.09795(6) 0.12800(9) 0.0548(4) Uani 1.00 C9 0.38351(7) 0.23180(6) 0.60277(8) 0.0474(4) Uani 1.00 C11 0.15635(8) 0.04245(6) 0.35658(8) 0.0490(4) Uani 1.00 C14 -0.18493(8) 0.17305(7) 0.26236(9) 0.0596(4) Uani 1.00 C15 -0.21350(9) 0.17678(6) 0.11667(9) 0.0578(4) Uani 1.00 C4 0.26153(7) 0.08767(6) 0.45673(8) 0.0456(4) Uani 1.00 C13 -0.06318(8) 0.13270(6) 0.34060(8) 0.0543(4) Uani 1.00 C16 -0.11980(10) 0.14003(7) 0.04948(8) 0.0599(5) Uani 1.00 C6 0.25096(8) 0.38054(6) 0.41630(9) 0.0556(4) Uani 1.00 C8 0.41206(8) 0.33667(7) 0.63146(9) 0.0581(4) Uani 1.00 C1 0.46544(8) 0.15647(7) 0.70053(9) 0.0553(4) Uani 1.00 C7 0.34594(9) 0.41089(7) 0.53960(10) 0.0618(5) Uani 1.00 C3 0.35770(8) 0.01694(6) 0.54500(9) 0.0519(4) Uani 1.00 H5 0.15318 0.25790 0.30331 0.05000 Uiso 1.00 H17 0.06601 0.07095 0.08160 0.05000 Uiso 1.00 H14 -0.25083 0.19915 0.30796 0.05000 Uiso 1.00 H15 -0.29850 0.20538 0.06237 0.05000 Uiso 1.00 H13 -0.04438 0.13070 0.44190 0.05000 Uiso 1.00 H16 -0.13940 0.14343 -0.05172 0.05000 Uiso 1.00 H6 0.20566 0.43174 0.34910 0.05000 Uiso 1.00 H8 0.47786 0.35657 0.71716 0.05000 Uiso 1.00 H7 0.36574 0.48289 0.55997 0.05000 Uiso 1.00 H20 0.2365 -0.08540 0.3873 0.050 Uiso 1.00 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 O2 C3 123.70(10) ? C5 C10 C9 116.60(10) ? C5 C10 C4 124.60(10) ? C9 C10 C4 118.70(10) ? C17 C12 C11 119.80(10) ? C17 C12 C13 119.20(10) ? C11 C12 C13 120.80(10) ? C10 C5 C6 121.30(10) ? C12 C17 C16 120.50(10) ? C10 C9 C8 121.50(10) ? C10 C9 C1 121.00(10) ? C8 C9 C1 117.40(10) ? O20 C11 C12 110.70(10) yes O20 C11 C4 122.80(10) yes C12 C11 C4 126.40(10) yes C15 C14 C13 120.10(10) ? C14 C15 C16 120.00(10) ? C10 C4 C11 126.50(10) yes C10 C4 C3 117.80(10) yes C11 C4 C3 115.80(10) yes C12 C13 C14 120.40(10) ? C17 C16 C15 119.80(10) ? C5 C6 C7 121.10(10) ? C9 C8 C7 120.50(10) ? O2 C1 O18 115.60(10) ? O2 C1 C9 117.60(10) ? O18 C1 C9 126.80(10) ? C6 C7 C8 119.00(10) ? O2 C3 O19 114.80(10) ? O2 C3 C4 119.80(10) ? O19 C3 C4 125.40(10) ? 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 O2 C1 . . 1.392(2) ? O2 C3 . . 1.357(2) ? O19 C3 . . 1.231(2) yes O20 C11 . . 1.329(2) yes O18 C1 . . 1.196(2) ? C10 C5 . . 1.404(2) ? C10 C9 . . 1.3980(10) ? C10 C4 . . 1.473(2) ? C12 C17 . . 1.386(2) ? C12 C11 . . 1.479(2) yes C12 C13 . . 1.380(2) ? C5 C6 . . 1.373(2) ? C17 C16 . . 1.378(2) ? C9 C8 . . 1.396(2) ? C9 C1 . . 1.461(2) ? C11 C4 . . 1.375(2) yes C14 C15 . . 1.381(2) ? C14 C13 . . 1.374(2) ? C15 C16 . . 1.378(2) ? C4 C3 . . 1.445(2) ? C6 C7 . . 1.388(2) ? C8 C7 . . 1.363(2) ? O19 H20 . . 1.61(2) 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 C1 O2 C3 O19 172.1(2) ? C3 O2 C1 O18 -176.9(2) ? C3 O2 C1 C9 1.20(10) ? C1 O2 C3 C4 -10.20(10) ? C9 C10 C5 C6 -1.50(10) ? C5 C10 C9 C8 2.80(10) ? C5 C10 C9 C1 -174.4(2) ? C5 C10 C4 C11 -14.70(10) ? C4 C10 C5 C6 -177.1(2) ? C5 C10 C4 C3 165.5(2) ? C9 C10 C4 C11 169.7(2) ? C4 C10 C9 C8 178.7(2) ? C4 C10 C9 C1 1.50(10) ? C9 C10 C4 C3 -10.10(10) ? C17 C12 C11 O20 -63.70(10) ? C17 C12 C11 C4 119.5(2) ? C11 C12 C17 C16 175.7(2) ? C17 C12 C13 C14 0.50(10) ? C13 C12 C17 C16 0.60(10) ? C13 C12 C11 O20 111.30(10) ? C11 C12 C13 C14 -174.5(2) ? C13 C12 C11 C4 -65.50(10) yes C10 C5 C6 C7 -0.90(10) ? C12 C17 C16 C15 -1.40(10) ? C10 C9 C8 C7 -1.80(10) ? C10 C9 C1 O2 3.20(10) ? C10 C9 C1 O18 -179.0(2) ? C8 C9 C1 O2 -174.1(2) ? C8 C9 C1 O18 3.70(10) ? C1 C9 C8 C7 175.5(2) ? O20 C11 C4 C10 170.1(2) ? O20 C11 C4 C3 -10.10(10) ? C12 C11 C4 C10 -13.40(10) yes C12 C11 C4 C3 166.4(2) ? C15 C14 C13 C12 -0.80(10) ? C13 C14 C15 C16 0.00(10) ? C14 C15 C16 C17 1.20(10) ? C10 C4 C3 O2 14.40(10) ? C10 C4 C3 O19 -168.1(2) ? C11 C4 C3 O2 -165.4(2) ? C11 C4 C3 O19 12.00(10) ? C5 C6 C7 C8 2.10(10) ? C9 C8 C7 C6 -0.70(10) ? H20 O19 C3 O2 173.7(4) ? H20 O19 C3 C4 -3.9(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21182880 2 PubChem 135460092