Dinuclear zinc catalyzed asymmetric spirannulation reaction: an umpolung strategy for formation of α-alkylated-α-hydroxyoxindoles.
Trost, Barry M.; Hirano, Keiichi; Organic letters 14 (2012) 2446–2449; doi:10.1021/ol300577y

data_1507667
_publ_section_title
;
 Dinuclear zinc catalyzed asymmetric spirannulation reaction: an umpolung
 strategy for formation of \a-alkylated-\a-hydroxyoxindoles.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2446
_journal_page_last               2449
_journal_paper_doi               10.1021/ol300577y
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H13 Br2 N O3'
_chemical_formula_sum            'C18 H13 Br2 N O3'
_chemical_formula_weight         451.11
_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                 91.624(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3956(8)
_cell_length_b                   13.8645(14)
_cell_length_c                   14.4310(15)
_cell_measurement_reflns_used    7675
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.43
_cell_volume                     1679.1(3)
_computing_cell_refinement       'Bruker SAINT v7.68A'
_computing_data_collection       'Bruker APEX-II v2010-7'
_computing_data_reduction        'Bruker SAINT v7.68A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of \w and \f-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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22046
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    4.844
_exptl_absorpt_correction_T_max  0.7613
_exptl_absorpt_correction_T_min  0.5599
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 3953 Friedel Pairs.'
_refine_ls_abs_structure_Flack   0.019(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8321
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                7384
_reflns_number_total             8321
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300577y_si_002.cif
_cod_data_source_block           su040
_cod_depositor_comments          'Adding full bibliography for 1507667.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1507667