#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011658.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_2011658 loop_ _publ_author_name 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Razak, Ibrahim Abdul' 'Saewon, Nisakorn' 'Karalai, Chatchanok' 'Chantrapromma, Kan' _publ_section_title ; 2-(4-Acetyl-3,5-dihydroxy-2-methylphenoxy)-4,6-dimethoxy-3-methylbenzoic acid ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e598 _journal_page_last e599 _journal_paper_doi 10.1107/S0108270100016280 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C19 H20 O8' _chemical_formula_weight 376.35 _chemical_melting_point 175.0(10) _chemical_name_systematic ; 2-(4-Acetyl-3,5-dihydroxy-2-methylphenoxy)-4,6-dimethoxy-3-methylbenzoic 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 SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.9280(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.0228(3) _cell_length_b 24.7920(10) _cell_length_c 12.1890(10) _cell_measurement_reflns_used 3937 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.15 _cell_measurement_theta_min 1.64 _cell_volume 1787.02(19) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_publication_material 'SHELXTL and PLATON (Spek, 1990)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .904 _diffrn_measured_fraction_theta_max .904 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0753 _diffrn_reflns_av_sigmaI/netI .1018 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6669 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.64 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .110 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light brown' _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 792 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .10 _refine_diff_density_max .47 _refine_diff_density_min -.36 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .961 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 2848 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .961 _refine_ls_R_factor_all .136 _refine_ls_R_factor_gt .080 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1483P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .231 _reflns_number_gt 1529 _reflns_number_total 2848 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0457.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '174-176' was changed to '175.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '174-176' was changed to '175.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1787.1(2) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2011658 _cod_database_fobs_code 2011658 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 1.1912(5) .58748(10) .2336(2) .0408(8) Uani d . 1 . . O O2 .5518(6) .65014(13) -.0280(3) .0714(12) Uani d . 1 . . O H2A .5548 .6186 -.0477 .107 Uiso calc R 1 . . H O3 .6996(7) .80722(13) .0786(3) .0742(12) Uani d . 1 . . O O4 1.0595(7) .77311(12) .1958(3) .0718(12) Uani d . 1 . . O H4A .9642 .7950 .1667 .108 Uiso calc R 1 . . H O5 .6954(6) .48547(12) .4075(3) .0585(10) Uani d . 1 . . O O6 1.1350(5) .39835(11) .1675(3) .0469(9) Uani d . 1 . . O O7 1.4470(5) .46170(12) .1015(3) .0482(9) Uani d . 1 . . O O8 1.2700(6) .53787(13) .0455(3) .0613(10) Uani d . 1 . . O H8A 1.3684 .5390 .0074 .092 Uiso calc R 1 . . H C1 .8631(8) .61821(17) .1042(4) .0462(12) Uani d . 1 . . C H1A .8223 .5829 .0843 .055 Uiso calc R 1 . . H C2 .7321(8) .66010(17) .0563(4) .0486(13) Uani d . 1 . . C C3 .7823(8) .71442(16) .0875(4) .0422(12) Uani d . 1 . . C C4 .9890(8) .72245(16) .1640(4) .0442(12) Uani d . 1 . . C C5 1.1305(8) .68091(16) .2101(4) .0425(12) Uani d . 1 . . C C6 1.0567(8) .62856(16) .1827(4) .0402(11) Uani d . 1 . . C C7 1.0854(7) .53831(15) .2480(4) .0336(10) Uani d . 1 . . C C8 .9357(7) .53618(16) .3208(4) .0400(11) Uani d . 1 . . C C9 .8464(7) .48542(17) .3387(4) .0396(11) Uani d . 1 . . C C10 .9128(7) .43905(16) .2901(4) .0402(11) Uani d . 1 . . C H10A .8545 .4057 .3052 .048 Uiso calc R 1 . . H C11 1.0657(7) .44248(16) .2190(4) .0359(10) Uani d . 1 . . C C12 1.1536(7) .49248(15) .1943(3) .0323(10) Uani d . 1 . . C C13 .6371(9) .76068(18) .0483(4) .0543(14) Uani d . 1 . . C C14 .4080(10) .7549(2) -.0252(5) .0721(17) Uani d . 1 . . C H14A .3408 .7899 -.0401 .108 Uiso calc R 1 . . H H14B .3133 .7330 .0119 .108 Uiso calc R 1 . . H H14C .4236 .7381 -.0943 .108 Uiso calc R 1 . . H C15 1.3484(9) .6915(2) .2918(5) .0708(17) Uani d . 1 . . C H15A 1.3722 .7297 .2999 .106 Uiso calc R 1 . . H H15B 1.4723 .6755 .2643 .106 Uiso calc R 1 . . H H15C 1.3389 .6760 .3630 .106 Uiso calc R 1 . . H C16 .8672(9) .58493(18) .3812(4) .0535(13) Uani d . 1 . . C H16A .9421 .6164 .3601 .080 Uiso calc R 1 . . H H16B .9095 .5796 .4604 .080 Uiso calc R 1 . . H H16C .7064 .5898 .3614 .080 Uiso calc R 1 . . H C17 .5833(9) .43585(19) .4250(5) .0658(16) Uani d . 1 . . C H17A .4812 .4420 .4754 .099 Uiso calc R 1 . . H H17B .6937 .4094 .4564 .099 Uiso calc R 1 . . H H17C .5001 .4230 .3549 .099 Uiso calc R 1 . . H C18 1.0217(9) .34841(17) .1762(5) .0560(14) Uani d . 1 . . C H18A 1.0858 .3210 .1362 .084 Uiso calc R 1 . . H H18B .8639 .3524 .1449 .084 Uiso calc R 1 . . H H18C 1.0393 .3383 .2534 .084 Uiso calc R 1 . . H C19 1.3050(8) .49644(16) .1123(4) .0384(11) Uani d . 1 . . C 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 O1 .0546(18) .0297(16) .038(2) -.0020(13) .0086(15) .0020(13) O2 .093(3) .0396(18) .070(3) .0101(18) -.013(2) -.0040(17) O3 .104(3) .032(2) .084(3) .0077(18) .011(2) .0013(18) O4 .100(3) .0298(18) .082(3) -.0069(18) .008(2) -.0062(17) O5 .079(2) .047(2) .061(3) .0046(17) .042(2) .0006(16) O6 .067(2) .0329(17) .048(2) .0005(14) .0296(17) -.0024(14) O7 .066(2) .0402(17) .045(2) .0076(16) .0263(17) .0050(14) O8 .084(2) .054(2) .057(2) .0194(18) .041(2) .0228(17) C1 .073(3) .025(2) .037(3) .003(2) .005(3) -.0011(19) C2 .067(3) .036(3) .039(3) -.001(2) .001(3) -.002(2) C3 .069(3) .029(2) .035(3) .002(2) .023(3) .0003(18) C4 .075(3) .026(2) .037(3) -.009(2) .022(3) -.0035(18) C5 .063(3) .031(2) .036(3) -.006(2) .016(2) -.0018(19) C6 .060(3) .032(2) .032(3) .002(2) .017(2) .0013(19) C7 .043(2) .032(2) .026(3) .0014(19) .005(2) .0047(17) C8 .056(3) .031(2) .034(3) .006(2) .013(2) .0014(19) C9 .051(3) .042(3) .032(3) .010(2) .023(2) .0045(19) C10 .056(3) .032(2) .036(3) .000(2) .019(2) .0052(19) C11 .052(2) .034(2) .025(3) .0054(19) .016(2) .0004(18) C12 .043(2) .036(2) .021(3) .0034(18) .014(2) .0046(17) C13 .091(4) .036(3) .042(3) .010(3) .026(3) .008(2) C14 .088(4) .051(3) .076(4) .018(3) .012(3) .012(3) C15 .079(4) .054(3) .076(4) -.011(3) .006(3) -.009(3) C16 .078(3) .043(3) .045(3) .007(2) .025(3) -.001(2) C17 .077(4) .053(3) .078(4) -.004(3) .043(3) .009(3) C18 .072(3) .039(3) .065(4) -.001(2) .034(3) -.004(2) C19 .061(3) .030(2) .025(3) -.001(2) .012(2) -.0003(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C6 O1 C7 117.3(3) yes C2 O2 H2A 109.5 ? C4 O4 H4A 109.5 ? C9 O5 C17 118.8(4) yes C11 O6 C18 117.9(3) yes C19 O8 H8A 109.5 ? C2 C1 C6 119.8(4) ? C2 C1 H1A 120.1 ? C6 C1 H1A 120.1 ? C1 C2 O2 119.7(4) ? C1 C2 C3 122.1(4) ? O2 C2 C3 118.1(4) ? C2 C3 C4 115.2(4) ? C2 C3 C13 124.9(4) ? C4 C3 C13 119.9(4) ? O4 C4 C5 115.9(4) ? O4 C4 C3 120.3(4) ? C5 C4 C3 123.8(4) ? C4 C5 C6 116.9(4) ? C4 C5 C15 121.9(4) ? C6 C5 C15 121.2(4) ? O1 C6 C1 121.5(4) ? O1 C6 C5 116.7(4) ? C1 C6 C5 121.8(4) ? C8 C7 O1 118.8(4) ? C8 C7 C12 123.4(4) ? O1 C7 C12 117.6(4) ? C7 C8 C9 116.8(4) ? C7 C8 C16 123.6(4) ? C9 C8 C16 119.6(4) ? O5 C9 C10 123.3(4) ? O5 C9 C8 114.8(4) ? C10 C9 C8 121.8(4) ? C11 C10 C9 119.8(4) ? C11 C10 H10A 120.1 ? C9 C10 H10A 120.1 ? O6 C11 C10 122.5(4) ? O6 C11 C12 116.6(4) ? C10 C11 C12 120.8(4) ? C11 C12 C7 117.2(4) ? C11 C12 C19 120.7(4) ? C7 C12 C19 122.1(4) ? O3 C13 C3 120.0(5) ? O3 C13 C14 117.1(4) ? C3 C13 C14 122.9(4) ? C13 C14 H14A 109.5 ? C13 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? C13 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? C5 C15 H15A 109.5 ? C5 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? C5 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? C8 C16 H16A 109.5 ? C8 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? C8 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? O5 C17 H17A 109.5 ? O5 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? O5 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? O6 C18 H18A 109.5 ? O6 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? O6 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? O7 C19 O8 121.0(4) ? O7 C19 C12 123.6(4) ? O8 C19 C12 115.3(4) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 . 1.374(5) yes O1 C7 . 1.402(5) yes O2 C2 . 1.369(6) yes O2 H2A . .8200 ? O3 C13 . 1.248(5) yes O4 C4 . 1.358(5) yes O4 H4A . .8200 ? O5 C9 . 1.349(5) yes O5 C17 . 1.438(5) yes O6 C11 . 1.366(5) yes O6 C18 . 1.427(5) yes O7 C19 . 1.239(5) yes O8 C19 . 1.303(5) yes O8 H8A . .8200 ? C1 C2 . 1.366(6) ? C1 C6 . 1.385(6) ? C1 H1A . .9300 ? C2 C3 . 1.416(6) ? C3 C4 . 1.421(7) ? C3 C13 . 1.466(6) ? C4 C5 . 1.386(6) ? C5 C6 . 1.392(6) ? C5 C15 . 1.512(7) ? C7 C8 . 1.381(6) ? C7 C12 . 1.411(6) ? C8 C9 . 1.402(6) ? C8 C16 . 1.512(6) ? C9 C10 . 1.387(6) ? C10 C11 . 1.381(6) ? C10 H10A . .9300 ? C11 C12 . 1.403(6) ? C12 C19 . 1.478(6) ? C13 C14 . 1.503(8) ? C14 H14A . .9600 ? C14 H14B . .9600 ? C14 H14C . .9600 ? C15 H15A . .9600 ? C15 H15B . .9600 ? C15 H15C . .9600 ? C16 H16A . .9600 ? C16 H16B . .9600 ? C16 H16C . .9600 ? C17 H17A . .9600 ? C17 H17B . .9600 ? C17 H17C . .9600 ? C18 H18A . .9600 ? C18 H18B . .9600 ? C18 H18C . .9600 ? 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 O2 H2A O7 3_765 .82 2.10 2.914(4) 178 yes O4 H4A O3 1_555 .82 1.77 2.506(6) 148 yes O8 H8A O7 3_865 .82 1.89 2.697(5) 170 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 O2 174.4(4) yes C6 C1 C2 C3 -2.7(7) ? C1 C2 C3 C4 5.6(7) yes O2 C2 C3 C4 -171.5(4) ? C1 C2 C3 C13 -173.3(4) ? O2 C2 C3 C13 9.6(7) yes C2 C3 C4 O4 177.0(4) yes C13 C3 C4 O4 -4.1(7) ? C2 C3 C4 C5 -2.6(7) ? C13 C3 C4 C5 176.3(4) yes O4 C4 C5 C6 177.2(4) yes C3 C4 C5 C6 -3.2(7) ? O4 C4 C5 C15 .7(7) ? C3 C4 C5 C15 -179.7(5) ? C7 O1 C6 C1 -29.9(6) yes C7 O1 C6 C5 152.9(4) ? C2 C1 C6 O1 179.2(4) ? C2 C1 C6 C5 -3.8(7) ? C4 C5 C6 O1 -176.3(4) yes C15 C5 C6 O1 .2(7) ? C4 C5 C6 C1 6.5(7) ? C15 C5 C6 C1 -177.0(5) ? C6 O1 C7 C8 -67.2(5) ? C6 O1 C7 C12 118.3(4) ? O1 C7 C8 C9 -175.6(4) ? C12 C7 C8 C9 -1.4(6) ? O1 C7 C8 C16 4.0(6) ? C12 C7 C8 C16 178.2(4) ? C17 O5 C9 C10 -5.1(7) yes C17 O5 C9 C8 175.9(4) yes C7 C8 C9 O5 -178.0(4) ? C16 C8 C9 O5 2.5(6) ? C7 C8 C9 C10 3.0(6) ? C16 C8 C9 C10 -176.5(4) ? O5 C9 C10 C11 179.0(4) ? C8 C9 C10 C11 -2.1(7) ? C18 O6 C11 C10 8.6(6) yes C18 O6 C11 C12 -169.9(4) ? C9 C10 C11 O6 -179.1(4) yes C9 C10 C11 C12 -.6(7) ? O6 C11 C12 C7 -179.3(4) ? C10 C11 C12 C7 2.2(6) ? O6 C11 C12 C19 2.8(6) ? C10 C11 C12 C19 -175.8(4) ? C8 C7 C12 C11 -1.2(6) ? O1 C7 C12 C11 173.1(3) ? C8 C7 C12 C19 176.7(4) yes O1 C7 C12 C19 -9.0(6) ? C2 C3 C13 O3 -178.2(5) ? C4 C3 C13 O3 3.0(7) ? C2 C3 C13 C14 3.8(8) yes C4 C3 C13 C14 -175.0(5) ? C11 C12 C19 O7 -36.4(6) ? C7 C12 C19 O7 145.8(4) ? C11 C12 C19 O8 139.3(4) ? C7 C12 C19 O8 -38.5(6) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105825 2 PubChem 139058063