Asymmetric dearomatization of 1-aminonaphthalene derivatives by gold-catalyzed intramolecular double C-C bond formation.
Oka, Junko; Okamoto, Ryuichi; Noguchi, Keiichi; Tanaka, Ken; Organic letters 17 (2015) 676–679; doi:10.1021/ol503698s

data_1518567
_publ_section_title
;
 Asymmetric dearomatization of 1-aminonaphthalene derivatives by
 gold-catalyzed intramolecular double C-C bond formation.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              676
_journal_page_last               679
_journal_paper_doi               10.1021/ol503698s
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 Br N O3'
_chemical_formula_sum            'C24 H22 Br N O3'
_chemical_formula_weight         452.34
_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
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9945(2)
_cell_length_b                   12.4644(2)
_cell_length_c                   17.7143(3)
_cell_measurement_reflns_used    34803
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.54
_cell_volume                     1985.97(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36532
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         4.34
_exptl_absorpt_coefficient_mu    3.035
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_correction_T_min  0.420
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881. 1549 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.020(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0434P)^2^+0.4274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0696
_reflns_number_gt                3477
_reflns_number_total             3630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503698s_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 1518565--1518567.cif.'
_cod_database_code               1518567