Total synthesis of natural p-quinol cochinchinenone.
Barradas, Silvia; Hernández-Torres, Gloria; Urbano, Antonio; Carreño, M Carmen; Organic letters 14 (2012) 5952–5955; doi:10.1021/ol302858r

data_1516097
_publ_section_title
;
 Total synthesis of natural p-quinol cochinchinenone.
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_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5952
_journal_page_last               5955
_journal_paper_doi               10.1021/ol302858r
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C11 H12 O5'
_chemical_formula_weight         224.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 109.962(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4253(3)
_cell_length_b                   12.8651(4)
_cell_length_c                   8.1381(3)
_cell_measurement_temperature    100.(2)
_cell_volume                     1025.92(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4695
_diffrn_reflns_theta_full        70.72
_diffrn_reflns_theta_max         70.72
_diffrn_reflns_theta_min         5.68
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.138
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.37(14)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.2415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                1728
_reflns_number_total             1748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302858r_si_002.cif
_cod_data_source_block           I
_cod_database_code               1516097