Chiral Hypervalent Organoiodine-Catalyzed Enantioselective Oxidative Spirolactonization of Naphthol Derivatives.
Uyanik, Muhammet; Yasui, Takeshi; Ishihara, Kazuaki; The Journal of organic chemistry 82 (2017) 11946–11953; doi:10.1021/acs.joc.7b01941

data_4032867
_publ_section_title
;
 Chiral Hypervalent Organoiodine-Catalyzed Enantioselective Oxidative
 Spirolactonization of Naphthol Derivatives.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11946
_journal_page_last               11953
_journal_paper_doi               10.1021/acs.joc.7b01941
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration (S)
_chemical_formula_sum            'C13 H9 Br O3'
_chemical_formula_weight         291.86
_chemical_name_common
; 
(S)-3'-bromo-2'H,3H-spiro[furan-2,1'-naphthalene]-2',5(4H)-dione
;
_space_group_IT_number           1
_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           SHELXL-97
_cell_angle_alpha                89.973(2)
_cell_angle_beta                 92.232(2)
_cell_angle_gamma                90.086(2)
_cell_formula_units_Z            8
_cell_length_a                   9.1853(12)
_cell_length_b                   18.882(2)
_cell_length_c                   13.3012(17)
_cell_measurement_reflns_used    13469
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      1.10
_cell_volume                     2305.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16830
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         1.08
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.558
_exptl_absorpt_correction_T_max  0.5364
_exptl_absorpt_correction_T_min  0.4149
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1309
_refine_ls_number_reflns         13469
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0645
_reflns_number_gt                11478
_reflns_number_total             13469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01941_si_002.cif
_cod_data_source_block           tyf1
_cod_depositor_comments
;
Adding full bibliography for 4032866--4032867.cif.

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P1
_cod_original_formula_sum        'C104 H72 Br8 O24'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     2344.90
_cod_database_code               4032867