(±)-2-Oxocyclohexanepropionic acid: dual conformational selection and hydrogen bonding in a δ-keto acid, and a two-phase technique for crystallizing acids by contact with aqueous solutions of their salts
Lalancette, Roger A.; Thompson, Hugh W.; Acta Crystallographica Section C 59 (2003) o638–o640; doi:10.1107/S0108270103020638

data_2013596
_publ_section_title
;
 (+-)-2-Oxocyclohexanepropionic acid: dual conformational selection and
 hydrogen bonding in a \d-keto acid, and a two-phase technique for
 crystallizing acids by contact with aqueous solutions of their salts
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o638
_journal_page_last               o640
_journal_paper_doi               10.1107/S0108270103020638
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C9 H14 O3'
_chemical_formula_moiety         'C9 H14 O3'
_chemical_formula_sum            'C9 H14 O3'
_chemical_formula_weight         170.20
_chemical_melting_point          340
_chemical_name_systematic
;
(+-)-2-Oxocyclohexanepropionic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                63.198(11)
_cell_angle_beta                 86.956(12)
_cell_angle_gamma                85.297(14)
_cell_formula_units_Z            4
_cell_length_a                   5.4302(9)
_cell_length_b                   13.370(2)
_cell_length_c                   14.075(2)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      10.5
_cell_measurement_theta_min      3.2
_cell_volume                     908.9(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens,1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXP97 in SHELXTL'
_computing_publication_material  'SHELXL97 in SHELXTL'
_computing_structure_refinement  'SHELXL97 in SHELXTL'
_computing_structure_solution    'SHELXS97 in SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2\q/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4166
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        'variation <1.5'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SHELXTL; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.14
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.089
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.1786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.126
_refine_ls_wR_factor_ref         0.145
_reflns_number_gt                1995
_reflns_number_total             3104
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1439.cif
_cod_data_source_block           I
_cod_depositor_comments
;
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 
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_cod_database_code               2013596
_cod_database_fobs_code          2013596