#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008461.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_2008461 loop_ _publ_author_name 'Gerkin, Roger E.' _publ_section_title ; 3-[2-(1,3-Dioxolan-2-yl)ethyl]-2-methylbenzoic acid ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 798 _journal_page_last 801 _journal_paper_doi 10.1107/S0108270199000128 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C13 H16 O4 ' _chemical_formula_sum 'C13 H16 O4' _chemical_formula_weight 236.27 _chemical_name_common '3-[2-(1,3-dioxolan-2-yl)ethyl]-2-methylbenzoic acid' _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.148(2) _cell_length_b 24.682(2) _cell_length_c 8.021(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 16.9 _cell_measurement_theta_min 12.5 _cell_volume 2405.0(7) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990)' _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type 'Rigaku AFC-5S' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2776 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% '+-1.8 (average maximum relative intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.10 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cut plate' _exptl_crystal_F_000 1008 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.47 _refine_diff_density_min -0.44 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.42 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 2776 _refine_ls_R_factor_gt 0.065 _refine_ls_shift/su_max 0.0002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/\s^2^(F^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .077 _reflns_number_gt 1169 _reflns_number_total 2776 _reflns_threshold_expression I>2\s~I~ _cod_data_source_file fr1181.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_adp_type' tag value 'Uij' was replaced with 'Uani' value 17 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 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_torsion_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/\s^2^(F^2^)' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/\s^2^(F^2^)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2405.0(8) _cod_database_code 2008461 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' '1/2-x, -y,1/2+z' ' -x, -y, -z' '1/2-x,1/2+y, +z' ' +x,1/2-y,1/2+z' '1/2+x, +y,1/2-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_calc_attached_atom O1 .4749(2) .49894(9) .2221(3) .0798(8) Uani ? ? O2 .4021(2) .45491(7) .0091(3) .0696(7) Uani ? ? O3 .05170(10) .19915(7) .2896(3) .0774(7) Uani ? ? O4 -.07780(10) .25881(7) .3667(2) .0677(6) Uani ? ? C1 .3263(2) .44110(10) .2826(4) .0517(9) Uani ? ? C2 .2390(2) .40690(9) .2364(4) .0531(9) Uani ? ? C3 .1688(2) .38777(10) .3626(4) .0540(9) Uani ? ? C4 .1883(2) .40160(10) .5271(4) .0630(10) Uani ? ? C5 .2745(2) .43480(10) .5711(4) .0636(10) Uani ? ? C6 .3432(2) .45480(10) .4495(4) .0584(10) Uani ? ? C7 .4031(2) .46460(10) .1573(4) .0566(10) Uani ? ? C8 .2180(2) .39050(10) .0574(4) .0830(10) Uani ? ? C9 .0729(2) .35008(10) .3262(3) .0639(10) Uani ? ? C10 .1074(2) .29086(10) .3273(3) .0577(9) Uani ? ? C11 .0181(2) .25360(10) .2699(4) .0588(10) Uani ? ? C12 -.0467(3) .16780(10) .3041(6) .0850(10) Uani ? ? C13 -.1328(3) .2076(2) .3566(6) .0930(10) Uani ? ? H1 .514(3) .5120(10) .138(4) .150(10) Uiso ? ? H4 .1396 .3874 .6142 .0752 Uiso calc C4 H5 .2868 .4441 .6883 .0763 Uiso calc C5 H6 .4043 .4787 .4801 .0700 Uiso calc C6 H8A .1938 .4221 -.0066 .0996 Uiso calc C8 H8B .2859 .3760 .0087 .0996 Uiso calc C8 H8C .1605 .3626 .0542 .0996 Uiso calc C8 H9A .0428 .3589 .2161 .0766 Uiso calc C9 H9B .0160 .3555 .4112 .0766 Uiso calc C9 H10A .1710 .2865 .2535 .0692 Uiso calc C10 H10B .1281 .2808 .4413 .0692 Uiso calc C10 H11 -.008(2) .2615(9) .144(3) .084(9) Uiso ? ? H12A -.069(3) .1570(10) .192(4) .170(10) Uiso ? ? H12B -.034(3) .1400(10) .378(4) .170(10) Uiso ? ? H13A -.184(2) .2100(10) .254(4) .140(10) Uiso ? ? H13B -.170(3) .1980(10) .461(5) .180(10) Uiso ? ? 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 .073(2) .098(2) .068(2) -.0380(10) .0030(10) .002(2) O2 .0710(10) .0730(10) .0650(10) -.0210(10) .0130(10) -.0020(10) O3 .0600(10) .0540(10) .119(2) -.0040(10) .0120(10) -.0080(10) O4 .0500(10) .0640(10) .0890(10) -.0050(10) .0080(10) -.0110(10) C1 .048(2) .044(2) .063(2) .0040(10) .007(2) .006(2) C2 .051(2) .048(2) .060(2) .0010(10) .005(2) .003(2) C3 .049(2) .040(2) .072(2) .0040(10) .007(2) .004(2) C4 .063(2) .052(2) .073(3) -.002(2) .019(2) .005(2) C5 .070(2) .058(2) .062(2) .000(2) .007(2) .001(2) C6 .052(2) .051(2) .072(2) -.0010(10) .002(2) .001(2) C7 .051(2) .048(2) .071(2) -.0010(10) .001(2) .004(2) C8 .075(2) .098(2) .075(3) -.035(2) .008(2) .001(2) C9 .056(2) .054(2) .082(2) -.0020(10) .012(2) .004(2) C10 .052(2) .053(2) .068(2) -.0060(10) .009(2) .004(2) C11 .058(2) .055(2) .063(2) .001(2) .004(2) .001(2) C12 .068(2) .072(2) .116(4) -.017(2) .007(3) -.009(3) C13 .060(2) .069(2) .150(4) -.017(2) .011(3) -.018(3) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart et al. (1965)' C .003 .002 'Creagh & McAuley (1992)' O .011 .006 'Creagh & McAuley (1992)' 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 107(2) no C11 O3 C12 106.4(2) yes C11 O4 C13 105.9(2) yes C2 C1 C6 120.6(3) no C2 C1 C7 122.0(3) yes C6 C1 C7 117.4(3) yes C1 C2 C3 118.0(3) no C1 C2 C8 122.6(3) no C3 C2 C8 119.4(3) no C2 C3 C4 120.0(3) no C2 C3 C9 122.2(3) no C4 C3 C9 117.8(3) no C3 C4 C5 121.5(3) no C3 C4 H4 119.3 no C5 C4 H4 119.3 no C4 C5 C6 119.6(3) no C4 C5 H5 120.2 no C6 C5 H5 120.2 no C1 C6 C5 120.3(3) no C1 C6 H6 119.9 no C5 C6 H6 119.9 no O1 C7 O2 121.2(3) yes O1 C7 C1 113.5(3) yes O2 C7 C1 125.3(3) yes C2 C8 H8A 109.5 no C2 C8 H8B 109.5 no C2 C8 H8C 109.5 no H8A C8 H8B 109.5 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no C3 C9 C10 112.1(2) no C3 C9 H9A 108.8 no C3 C9 H9B 108.8 no C10 C9 H9A 108.8 no C10 C9 H9B 108.8 no H9A C9 H9B 109.5 no C9 C10 C11 112.9(2) no C9 C10 H10A 108.6 no C9 C10 H10B 108.6 no C11 C10 H10A 108.6 no C11 C10 H10B 108.6 no H10A C10 H10B 109.5 no O3 C11 O4 105.4(2) yes O3 C11 C10 109.9(2) yes O3 C11 H11 111.0(10) no O4 C11 C10 112.0(2) yes O4 C11 H11 104.0(10) no C10 C11 H11 113.0(10) no O3 C12 C13 104.7(3) yes O3 C12 H12A 108(2) no O3 C12 H12B 108(2) no C13 C12 H12A 104(2) no C13 C12 H12B 115(2) no H12A C12 H12B 115(2) no O4 C13 C12 105.6(3) yes O4 C13 H13A 105.0(10) no O4 C13 H13B 112(2) no C12 C13 H13A 103.0(10) no C12 C13 H13B 113(2) no H13A C13 H13B 114(2) no 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 O1 C7 ? ? 1.322(3) yes O1 H1 ? ? .89(3) no O2 C7 ? ? 1.213(3) yes O3 C11 ? ? 1.413(3) yes O3 C12 ? ? 1.428(4) yes O4 C11 ? ? 1.406(3) yes O4 C13 ? ? 1.432(4) yes C1 C2 ? ? 1.405(3) no C1 C6 ? ? 1.396(3) no C1 C7 ? ? 1.489(3) no C2 C3 ? ? 1.405(3) no C2 C8 ? ? 1.513(4) no C3 C4 ? ? 1.383(4) no C3 C9 ? ? 1.520(3) no C4 C5 ? ? 1.375(3) no C4 H4 ? ? .980 no C5 C6 ? ? 1.376(3) no C5 H5 ? ? .980 no C6 H6 ? ? .980 no C8 H8A ? ? .980 no C8 H8B ? ? .980 no C8 H8C ? ? .980 no C9 C10 ? ? 1.521(3) no C9 H9A ? ? .980 no C9 H9B ? ? .980 no C10 C11 ? ? 1.495(3) no C10 H10A ? ? .980 no C10 H10B ? ? .980 no C11 H11 ? ? 1.07(2) no C12 C13 ? ? 1.495(5) no C12 H12A ? ? .98(3) no C12 H12B ? ? .92(3) no C13 H13A ? ? 1.04(3) no C13 H13B ? ? .98(4) no 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 5_665 0.89(3) 1.76(3) 2.639(3) 172(3) yes C11 H11 O4 7_554 1.07(2) 2.44(2) 3.451(4) 157(2) yes C4 H4 O3 7_555 0.98 2.77 3.656(3) 150 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 C11 O3 C12 C13 21.0(4) y O3 C12 C13 O4 -0.6(4) y C11 O4 C13 C12 -20.2(4) y C13 O4 C11 O3 33.8(3) y C12 O3 C11 O4 -34.4(3) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 100980227