(±)-3-Oxo-1,2,3,9,10,10a-hexahydrophenanthrene-10a-carboxylic acid: catemeric hydrogen bonding in a δ-keto acid
Miller, Alan J.; Brunskill, Andrew P. J.; Lalancette, Roger A.; Thompson, Hugh W.; Acta Crystallographica Section C 55 (1999) 563–566; doi:10.1107/S0108270198017417

data_2008347
_publ_section_title
;
 (+-)-3-Oxo-1,2,3,9,10,10a-hexahydrophenanthrene-10a-carboxylic acid:
 catemeric hydrogen bonding in a \d-keto acid
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              563
_journal_page_last               566
_journal_paper_doi               10.1107/S0108270198017417
_journal_volume                  55
_journal_year                    1999
_chemical_formula_analytical     'C15 H14 O3'
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_structural     'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_chemical_melting_point          'Decomposes above 420 K'
_chemical_name_common
;
(+/-)-10a-Carboxy-1,9,10,10a-tetrahydrophenanthren-3(2H)-one
;
_chemical_name_systematic
;
(+/-)-10a-Carboxy-1,9,10,10a-tetrahydrophenanthren-3(2H)-one
;
_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'
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                90.00
_cell_angle_beta                 101.79(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.305(2)
_cell_length_b                   12.780(3)
_cell_length_c                   10.444(3)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.82
_cell_measurement_theta_min      2.53
_cell_volume                     1215.8(5)
_computing_cell_refinement       'XSCANS (Siemens,  1996)'
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        'XSCANS (Siemens,  1996)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2\q/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.062
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3110
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        'variation <1'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   'face-indexed numerical (Sheldrick, 1994)'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      1.320(10)
_exptl_crystal_density_method    'flotation in CCl~4~/p-xylene'
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.162
_refine_ls_extinction_coef       'refined to 0'
_refine_ls_extinction_method     SHELXTL/PC
_refine_ls_goodness_of_fit_all   1.04
_refine_ls_goodness_of_fit_obs   1.16
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_restrained_S_obs      1.16
_refine_ls_R_factor_all          0.123
_refine_ls_R_factor_obs          0.059
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.5421P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.138
_refine_ls_wR_factor_obs         0.109
_reflns_number_observed          1304
_reflns_number_total             2393
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            fg1524.cif
_cod_data_source_block           FG1524
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

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

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.5421P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.5421P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2008347