(+)-2-(1,2,3,4,4a,5,6,7-Octahydro-4a,8-dimethyl-7-oxo-2-naphthyl)propionic acid: catemeric hydrogen bonding in a bicyclic sesquiterpenoid keto acid
Brunskill, Andrew P. J.; Thompson, Hugh W.; Lalancette, Roger A.; Acta Crystallographica Section C 58 (2002) o251–o253; doi:10.1107/S0108270102004365

data_2012696
_publ_section_title
;
 (+)-2-(1,2,3,4,4a,5,6,7-Octahydro-4a,8-dimethyl-7-oxo-2-naphthyl)propionic
 acid: catemeric hydrogen bonding in a bicyclic sesquiterpenoid keto
 acid
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o251
_journal_page_last               o253
_journal_paper_doi               10.1107/S0108270102004365
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C15 H22 O3'
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.33
_chemical_melting_point          398
_chemical_name_common            '(-)-3-oxo-11\a(H)-eudesm-4-en-12-oic acid'
_chemical_name_systematic
;
(+)-2-(1,2,3,4,4a,5,6,7-Octahydro-4a,8-dimethyl-7-oxo-2-
naphthyl)propionic acid
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 110.758(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0225(14)
_cell_length_b                   14.862(2)
_cell_length_c                   10.0873(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      13.8
_cell_measurement_theta_min      4.5
_cell_volume                     1405.0(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.029
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5441
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        'variation < 1.5'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.10
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.061
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.1708P]where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                1977
_reflns_number_total             2579
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1365.cif
_cod_data_source_block           I
_cod_original_cell_volume        1405.0(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2012696
_cod_database_fobs_code          2012696