Enantioselective Construction of Functionalized Tetrahydrocarbazoles Enabled by Asymmetric Relay Catalysis of Gold Complex and Chiral Brønsted Acid.
Zhao, Feng; Li, Nan; Zhu, Yi-Fan; Han, Zhi-Yong; Organic letters 18 (2016) 1506–1509; doi:10.1021/acs.orglett.6b00012

data_1543009
_publ_section_title
;
 Enantioselective Construction of Functionalized Tetrahydrocarbazoles
 Enabled by Asymmetric Relay Catalysis of Gold Complex and Chiral
 Br\/onsted Acid.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1506
_journal_page_last               1509
_journal_paper_doi               10.1021/acs.orglett.6b00012
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H16 Br N O2'
_chemical_formula_weight         346.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 107.684(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1594(6)
_cell_length_b                   11.9897(5)
_cell_length_c                   12.8474(8)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.4600
_cell_measurement_theta_min      3.7780
_cell_volume                     1490.97(15)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16450
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.071
_diffrn_reflns_theta_min         3.355
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.244
_refine_ls_abs_structure_details
;
 Flack x determined using 1713 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.027(6)
_refine_ls_extinction_coef       0.065(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6892
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0947P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1778
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                4684
_reflns_number_total             6892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00012_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               1543009
_shelx_estimated_absorpt_t_min   0.383
_shelx_estimated_absorpt_t_max   0.445
_shelxl_version_number           2013-4
_shelx_res_checksum              22886
_shelx_hkl_checksum              34761