Catalytic Enantioselective Intramolecular Redox Reactions: Ring-Fused Tetrahydroquinolines
Sandip Murarka; Indubhusan Deb; Chen Zhang; Daniel Seidel; Journal of the American Chemical Society 131 (2009) 13226–13227; doi:10.1021/ja905213f

data_4105038
_publ_section_title
;
 Catalytic Enantioselective Intramolecular Redox Reactions: Ring-Fused
 Tetrahydroquinolines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13226
_journal_page_last               13227
_journal_paper_doi               10.1021/ja905213f
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H19 Br N2 O3'
_chemical_formula_weight         427.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5391(8)
_cell_length_b                   10.8776(15)
_cell_length_c                   29.488(4)
_cell_measurement_reflns_used    3341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.12
_cell_measurement_theta_min      2.76
_cell_volume                     1776.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            5941
_diffrn_reflns_theta_full        32.10
_diffrn_reflns_theta_max         32.10
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    2.339
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SAINT (XPREP)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       rod
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                5428
_reflns_number_total             5941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905213f_si_001.cif
_cod_data_source_block           in225br
_cod_database_code               4105038