(<b>±</b>)-3-Oxocyclohexanecarboxylic and -acetic acids: contrasting hydrogen-bonding patterns in two homologous keto acids
Barcon, Alan; Brunskill, Andrew P. J.; Lalancette, Roger A.; Thompson, Hugh W.; Acta Crystallographica Section C 58 (2002) o154–o156; doi:10.1107/S0108270101020595

data_2012569
_publ_section_title
;
 (<b>+-</b>)-3-Oxocyclohexanecarboxylic and -acetic acids: contrasting
 hydrogen-bonding patterns in two homologous keto acids
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o154
_journal_page_last               o156
_journal_paper_doi               10.1107/S0108270101020595
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C8 H12 O3'
_chemical_formula_sum            'C8 H12 O3'
_chemical_formula_weight         156.18
_chemical_melting_point          351
_chemical_name_common            'cyclohexanone-3-acetic acid'
_chemical_name_systematic        '(+-)-3-Oxocyclohexaneacetic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 90.33(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.625(2)
_cell_length_b                   5.6690(10)
_cell_length_c                   21.841(5)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    241(2)
_cell_measurement_theta_max      13.0
_cell_measurement_theta_min      7.5
_cell_volume                     820.3(3)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXP(??)97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      241(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .032
_diffrn_reflns_av_sigmaI/netI    .039
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2238
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        'variation < 2'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             336
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .33
_refine_diff_density_max         .23
_refine_diff_density_min         -.12
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          .085
_refine_ls_R_factor_gt           .054
_refine_ls_shift/su_max          .02
_refine_ls_shift/su_mean         .00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.2424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .126
_refine_ls_wR_factor_ref         .143
_reflns_number_gt                989
_reflns_number_total             1447
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1356.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012569
_cod_database_fobs_code          2012569