(±)-3-Oxocyclopentanecarboxylic acid: the smallest keto acid known to aggregate by catemeric hydrogen bonding
Malak, Muhammad H.; Baker, Daniel; Brunskill, Andrew P. J.; Thompson, Hugh W.; Lalancette, Roger A.; Acta Crystallographica Section C 62 (2006) o669–o670; doi:10.1107/S0108270106041369

data_2015669
_publ_section_title
;
 (+-)-3-Oxocyclopentanecarboxylic acid: the smallest keto acid known to
 aggregate by catemeric hydrogen bonding
;
_journal_coeditor_code           AV3038
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o669
_journal_page_last               o670
_journal_paper_doi               10.1107/S0108270106041369
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H8 O3'
_chemical_formula_moiety         'C6 H8 O3'
_chemical_formula_sum            'C6 H8 O3'
_chemical_formula_weight         128.12
_chemical_melting_point          335
_chemical_name_systematic
;
(+-)-3-Oxocyclopentanecarboxylic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.862(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8564(8)
_cell_length_b                   7.9812(8)
_cell_length_c                   10.1367(10)
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.90
_cell_measurement_theta_min      2.57
_cell_volume                     589.90(10)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4895
_diffrn_reflns_theta_full        67.90
_diffrn_reflns_theta_max         67.90
_diffrn_reflns_theta_min         6.07
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.12
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.037
_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^)+(0.0437P)^2^+0.3094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.092
_refine_ls_wR_factor_ref         0.093
_reflns_number_gt                985
_reflns_number_total             1027
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            av3038.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015669
_cod_database_fobs_code          2015669