4-Oxocyclohexaneacetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enantiomer in an achiral ε-keto acid
Barcon, Alan; Brunskill, Andrew P. J.; Lalancette, Roger A.; Thompson, Hugh W.; Acta Crystallographica Section E 66 (2010) o2576–o2577; doi:10.1107/S1600536810036652

data_2227996
_publ_section_title
;
 4-Oxocyclohexaneacetic acid: catemeric hydrogen bonding and
 spontaneous resolution of a single conformational enantiomer in an
 achiral \e-keto acid
;
_journal_coeditor_code           SJ5037
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2576
_journal_page_last               o2577
_journal_paper_doi               10.1107/S1600536810036652
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H12 O3'
_chemical_formula_moiety         'C8 H12 O3'
_chemical_formula_sum            'C8 H12 O3'
_chemical_formula_weight         156.18
_chemical_melting_point          345
_chemical_name_systematic
;
4-Oxocyclohexaneacetic acid
;
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8531(12)
_cell_length_b                   6.8531(12)
_cell_length_c                   17.372(3)
_cell_measurement_reflns_used    6759
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.54
_cell_measurement_theta_min      5.09
_cell_volume                     815.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008<i>b</i>)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008<i>b</i>)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008<i>b</i>)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008<i>b</i>)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.017
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6963
_diffrn_reflns_theta_full        70.82
_diffrn_reflns_theta_max         70.82
_diffrn_reflns_theta_min         6.46
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  0.8822
_exptl_absorpt_correction_T_min  0.8063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008<i>a</i>)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 559 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008b)'
_refine_ls_goodness_of_fit_ref   1.18
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1310
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.18
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max_lt       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^)+(0.0369P)^2^+0.6710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.108
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                1274
_reflns_number_total             1310
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sj5037.cif
_cod_data_source_block           I
_cod_original_cell_volume        815.9(3)
_cod_database_code               2227996
_cod_database_fobs_code          2227996