Asymmetric Dearomatizing Spirolactonization of Naphthols Catalyzed by Spirobiindane-Based Chiral Hypervalent Iodine Species
Toshifumi Dohi; Naoko Takenaga; Tomofumi Nakae; Yosuke Toyoda; Mikio Yamasaki; Motoo Shiro; Hiromichi Fujioka; Akinobu Maruyama; Yasuyuki Kita; Journal of the American Chemical Society 135 (2013) 4558–4566; doi:10.1021/ja401074u

data_4119494
_publ_section_title
;
 Asymmetric Dearomatizing Spirolactonization of Naphthols Catalyzed by
 Spirobiindane-Based Chiral Hypervalent Iodine Species
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4558
_journal_page_last               4566
_journal_paper_doi               10.1021/ja401074u
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H9 Br O3'
_chemical_formula_sum            'C13 H9 Br O3'
_chemical_formula_weight         293.12
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.4341(6)
_cell_length_b                   10.1557(12)
_cell_length_c                   20.159(2)
_cell_measurement_reflns_used    3820
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.60
_cell_volume                     1112.5(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18015
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.697
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_description       platelet
_exptl_crystal_F_000             584.00
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.680
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1523 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.019(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0413P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                2333
_reflns_number_total             2532
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja401074u_si_002.cif
_cod_data_source_block           rgk1860
_cod_original_cell_volume        1112.5(3)
_cod_database_code               4119494