#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008544.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_2008544 loop_ _publ_author_name 'Henning Osholm S\/orensen' 'Andr\'e Collet' 'Sine Larsen' _publ_section_title ; (R)-(+)-2-(4-Chlorophenoxy)propionic acid ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 953 _journal_page_last 956 _journal_paper_doi 10.1107/S0108270199002280 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C9 H9 Cl O3' _chemical_formula_sum 'C9 H9 Cl O3' _chemical_formula_weight 200.61 _chemical_melting_point 376 _chemical_name_systematic ; (R)-(+)-2-(4-Chlorophenoxy)propionic acid ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90.00 _cell_angle_beta 104.45 _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.377(2) _cell_length_b 6.972(3) _cell_length_c 10.514(16) _cell_measurement_reflns_used 20 _cell_measurement_temperature 122.0(2) _cell_measurement_theta_max 43.62 _cell_measurement_theta_min 40.29 _cell_volume 452.7(7) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_data_reduction 'DREAM (Blessing, 1987)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 122.0(5) _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 CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.015 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3805 _diffrn_reflns_theta_full 74.92 _diffrn_reflns_theta_max 74.92 _diffrn_reflns_theta_min 4.34 _diffrn_standards_decay_% 3.7 _diffrn_standards_interval_time 167 _diffrn_standards_number 5 _exptl_absorpt_coefficient_mu 3.520 _exptl_absorpt_correction_T_max 0.782 _exptl_absorpt_correction_T_min 0.392 _exptl_absorpt_correction_type 'gaussian integration method' _exptl_absorpt_process_details '(DeTitta, 1985)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.214 _refine_diff_density_min -0.199 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.003(11) _refine_ls_extinction_coef 0.0105(12) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1854 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.022 _refine_ls_R_factor_gt 0.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.0899P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.062 _reflns_number_gt 1854 _reflns_number_total 1854 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf1292.cif _cod_data_source_block fh392 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2008544 _cod_database_fobs_code 2008544 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl .61756(5) .57888(5) .21421(3) .02860(11) Uani d . 1 . . Cl O7 -.17550(16) .51043(13) -.21134(9) .0183(2) Uani d . 1 . . O O10 -.00501(18) .43947(14) -.50413(10) .0235(2) Uani d . 1 . . O O11 -.11624(16) .23099(14) -.37467(10) .0200(2) Uani d . 1 . . O H11 -.068(3) .144(3) -.422(2) .030 Uiso d . 1 . . H C1 .0201(2) .52238(18) -.11982(13) .0162(2) Uani d . 1 . . C C2 .0111(2) .48176(18) .00854(13) .0178(3) Uani d . 1 . . C H2 -.120(3) .438(3) .0216(19) .031(5) Uiso d . 1 . . H C3 .1936(2) .4991(2) .11068(13) .0202(3) Uani d . 1 . . C H3 .191(3) .472(3) .2014(19) .026(5) Uiso d . 1 . . H C4 .3875(2) .5559(2) .08419(13) .0197(3) Uani d . 1 . . C C5 .4004(2) .5933(2) -.04267(13) .0204(2) Uani d . 1 . . C H5 .529(4) .628(3) -.0601(19) .035(5) Uiso d . 1 . . H C6 .2155(2) .5754(2) -.14609(12) .0191(2) Uani d . 1 . . C H6 .229(3) .600(3) -.2311(18) .028(4) Uiso d . 1 . . H C121 -.4213(2) .5893(3) -.41180(13) .0250(3) Uani d . 1 . . C H121 -.445(3) .615(3) -.506(2) .037(5) Uiso d . 1 . . H H122 -.479(3) .703(3) -.369(2) .029(5) Uiso d . 1 . . H H123 -.504(3) .474(3) -.402(2) .028(5) Uiso d . 1 . . H C8 -.1827(2) .5611(2) -.34341(12) .0173(2) Uani d . 1 . . C H81 -.110(3) .679(3) -.3478(17) .018(4) Uiso d . 1 . . H C9 -.0893(2) .40516(19) -.41416(12) .0155(2) 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 Cl .02565(17) .0359(2) .02103(16) .00023(14) -.00023(11) -.00384(15) O7 .0203(4) .0212(4) .0144(4) -.0020(3) .0065(3) -.0008(3) O10 .0362(5) .0163(4) .0233(5) -.0005(4) .0171(4) .0014(4) O11 .0297(5) .0129(4) .0207(5) .0001(4) .0125(4) .0009(4) C1 .0194(6) .0135(5) .0161(5) .0007(4) .0052(5) -.0022(4) C2 .0220(6) .0151(6) .0193(6) .0002(5) .0108(5) .0005(5) C3 .0295(7) .0170(6) .0158(6) .0027(5) .0091(5) .0007(5) C4 .0231(6) .0166(6) .0179(6) .0013(5) .0024(5) -.0017(5) C5 .0199(6) .0200(6) .0226(6) -.0001(5) .0078(5) -.0006(6) C6 .0230(6) .0201(6) .0164(5) -.0010(6) .0088(4) -.0011(6) C121 .0239(6) .0293(7) .0213(6) .0084(7) .0048(5) .0013(7) C8 .0224(6) .0158(6) .0148(5) .0006(5) .0066(4) .0006(5) C9 .0163(6) .0158(6) .0134(6) -.0001(4) .0019(4) .0010(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 C1 O7 C8 118.09(11) yes C9 O11 H11 111.2(14) no O7 C1 C6 125.32(13) yes O7 C1 C2 114.58(13) yes C6 C1 C2 120.08(13) no C3 C2 C1 120.38(14) no C3 C2 H2 121.9(12) no C1 C2 H2 117.7(12) no C2 C3 C4 119.28(14) no C2 C3 H3 121.8(12) no C4 C3 H3 118.9(12) no C5 C4 C3 121.14(12) no C5 C4 Cl 119.86(12) no C3 C4 Cl 119.00(12) yes C4 C5 C6 119.53(13) no C4 C5 H5 121.0(13) no C6 C5 H5 119.5(13) no C1 C6 C5 119.55(13) no C1 C6 H6 122.5(11) no C5 C6 H6 117.9(11) no C8 C121 H121 112.7(12) no C8 C121 H122 108.5(11) no H121 C121 H122 108.9(18) no C8 C121 H123 110.3(12) no H121 C121 H123 107.8(18) no H122 C121 H123 108.6(15) no O7 C8 C9 112.27(12) yes O7 C8 C121 106.11(11) yes C9 C8 C121 109.15(12) yes O7 C8 H81 111.4(10) no C9 C8 H81 109.9(10) no C121 C8 H81 107.8(10) no O10 C9 O11 123.04(12) yes O10 C9 C8 122.70(12) yes O11 C9 C8 114.19(12) yes 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 Cl C4 . 1.7455(18) yes O7 C1 . 1.3747(18) yes O7 C8 . 1.423(2) yes O10 C9 . 1.222(2) yes O11 C9 . 1.3085(17) yes O11 H11 . .89(2) no C1 C6 . 1.3921(18) no C1 C2 . 1.394(3) no C2 C3 . 1.378(2) no C2 H2 . .93(2) no C3 C4 . 1.391(2) no C3 H3 . .977(19) no C4 C5 . 1.382(3) no C5 C6 . 1.396(2) no C5 H5 . .92(2) no C6 H6 . .935(18) no C121 C8 . 1.5248(18) yes C121 H121 . .98(2) no C121 H122 . 1.03(2) no C121 H123 . .98(2) no C8 C9 . 1.5204(19) yes C8 H81 . .953(19) 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 O11 H11 O10 2_644 0.89(2) 1.74(2) 2.6161(19) 168(2) C8 H81 O10 2_554 0.953(19) 2.611(19) 3.452(2) 147.3(14) C2 H2 Cl 1_455 0.93(2) 3.094(19) 3.760(3) 130.1(16) C121 H121 Cl 1_454 0.98(2) 3.08(2) 4.002(6) 157.9(17) 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 O7 C8 -1.90(18) no C2 C1 O7 C8 176.24(11) yes O7 C1 C2 C3 -176.34(11) no C6 C1 C2 C3 1.9(2) no C1 C2 C3 C4 -0.6(2) no C2 C3 C4 C5 -0.6(2) no C2 C3 C4 Cl 179.63(11) no C3 C4 C5 C6 0.5(2) no Cl C4 C5 C6 -179.75(12) no O7 C1 C6 C5 176.04(12) yes C2 C1 C6 C5 -2.0(2) no C4 C5 C6 C1 0.8(2) no C1 O7 C8 C9 76.52(13) yes C1 O7 C8 C121 -164.32(11) yes O7 C8 C9 O10 -151.75(13) yes C121 C8 C9 O10 90.88(16) yes O7 C8 C9 O11 31.36(15) yes C121 C8 C9 O11 -86.01(15) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 643211 2 PubChem 736071