The epimeric 9-oxobicyclo[3.3.1]nonane-3-carboxylic acids: hydrogen-bonding patterns of the <i>endo</i> acid and the lactol of the <i>exo</i> acid
Papadakis, Markos M.; Pavon, Jorge A.; Lalancette, Roger A.; Thompson, Hugh W.; Acta Crystallographica Section C 59 (2003) o167–o170; doi:10.1107/S0108270103001495

data_2013148
_publ_section_title
;
 The epimeric 9-oxobicyclo[3.3.1]nonane-3-carboxylic acids:
 hydrogen-bonding patterns of the <i>endo</i> acid and the lactol of
 the <i>exo</i> acid
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o167
_journal_page_last               o170
_journal_paper_doi               10.1107/S0108270103001495
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C10 H14 O3'
_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_weight         182.21
_chemical_melting_point          404
_chemical_name_systematic
;
9-oxobicyclo[3.3.1]nonane-3\a-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                71.470(10)
_cell_angle_beta                 73.44(2)
_cell_angle_gamma                77.290(10)
_cell_formula_units_Z            2
_cell_length_a                   6.6170(10)
_cell_length_b                   7.3160(10)
_cell_length_c                   10.421(2)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      9.9
_cell_measurement_theta_min      3.3
_cell_volume                     453.81(14)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.020
_diffrn_reflns_av_sigmaI/netI    0.041
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2040
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        'variation < 1.1'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(SHELXTL; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'pentagonal rod'
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.0479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.095
_refine_ls_wR_factor_ref         0.108
_reflns_number_gt                1141
_reflns_number_total             1588
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1406.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 
;
_cod_original_cell_volume        453.81(13)
_cod_database_code               2013148
_cod_database_fobs_code          2013148