(+)- and (±)-ketopinic acid: hydrogen-bonding patterns in a β-keto acid in its enantiomeric and racemic forms and enantiomeric disordering in the racemate
Lalancette, Roger A.; Coté, Marie L.; Smith III, William J.; Thompson, Hugh W.; Vanderhoff, Peggy A.; Brunskill, Andrew P. J.; Campana, Charles; Burshtein, Izya; Rose, John P.; Acta Crystallographica Section C 55 (1999) 1600–1605; doi:10.1107/S0108270199007428

data_2008891
_publ_section_title
;
 (+)- and (+-)-ketopinic acid: hydrogen-bonding patterns in a \b-keto
 acid in its enantiomeric and racemic forms and enantiomeric
 disordering in the racemate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1600
_journal_page_last               1605
_journal_paper_doi               10.1107/S0108270199007428
_journal_volume                  55
_journal_year                    1999
_chemical_formula_analytical     'C10 H14 O3'
_chemical_formula_moiety         'C10 H14 O3'
_chemical_formula_structural     'C10 H14 O3'
_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_weight         182.21
_chemical_melting_point          511
_chemical_name_common            '(+/-)-ketopinic acid'
_chemical_name_systematic
'(+/-)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic 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'
_audit_creation_method           SHELXTL
_cell_angle_alpha                72.0130(10)
_cell_angle_beta                 77.0190(10)
_cell_angle_gamma                86.5460(10)
_cell_formula_units_Z            4
_cell_length_a                   7.0947(3)
_cell_length_b                   11.8316(6)
_cell_length_c                   12.1662(6)
_cell_measurement_reflns_used    4280
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.80
_cell_volume                     946.47(8)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device       'Siemens SMART CCD'
_diffrn_measurement_method
;
10s per frame, 1321 frames, 0.3\% \w oscillation
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            5796
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      1.260(10)
_exptl_crystal_density_method    'flotation in cyclohexane/CCl~4~'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max          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^)+(0.0615P)^2^+0.3444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.137
_reflns_number_gt                3710
_reflns_number_total             4161
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg1548.cif
_cod_data_source_block           II
_cod_database_code               2008891