Hydrogen bonding in enantiomeric <i>versus</i> racemic mono-carboxylic acids; a case study of 2-phenoxypropionic acid
Sørensen, Henning Osholm; Larsen, Sine; Acta Crystallographica Section B 59 (2003) 132–140; doi:10.1107/S0108768102022085

data_2103855
_publ_section_title
;
 Hydrogen bonding in enantiomeric <i>versus</i> racemic mono-carboxylic
 acids; a case study of 2-phenoxypropionic acid
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              132
_journal_page_last               140
_journal_paper_doi               10.1107/S0108768102022085
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17
_chemical_melting_point          388
_chemical_name_systematic
;
 (+-)-phenoxypropionic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 and manuel editing'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.816(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.781(3)
_cell_length_b                   5.2554(8)
_cell_length_c                   10.9534(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    122.4(5)
_cell_measurement_theta_max      41.89
_cell_measurement_theta_min      39.24
_cell_volume                     1641.4(4)
_computing_cell_refinement       'Enraf-Nonius Express (1994)'
_computing_data_collection       'Enraf-Nonius Express (1994)'
_computing_data_reduction        'DREAR (Blessing, 1987)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122.4(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6057
_diffrn_reflns_theta_full        74.84
_diffrn_reflns_theta_max         74.84
_diffrn_reflns_theta_min         3.10
_diffrn_standards_decay_%        5.8
_diffrn_standards_interval_time  166.7
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(DeTitta, 1985)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.224
_refine_ls_extinction_coef       0.0066(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+1.2118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                1624
_reflns_number_total             1697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            os0103.cif
_cod_data_source_block           racemic
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2103855