Total Synthesis of Chlorocyclinone A, a PPAR-γ Antagonist
Raju Karmakar; Dipakranjan Mal; Journal of Organic Chemistry 77 (2012) 10235–10248; doi:10.1021/jo301712b

data_4027709
_publ_section_title
;
 Total Synthesis of Chlorocyclinone A, a PPAR-\g Antagonist
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10235
_journal_page_last               10248
_journal_paper_doi               10.1021/jo301712b
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.24
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 96.988(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.407(3)
_cell_length_b                   13.388(3)
_cell_length_c                   11.634(3)
_cell_measurement_reflns_used    6037
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.02
_cell_volume                     2381.9(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6037
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  25.00
_exptl_absorpt_correction_T_min  2.02
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.861
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1181P)^2^+3.3899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                1781
_reflns_number_total             2089
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo301712b_si_003.cif
_cod_data_source_block           rajuout
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               4027709