One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.
Liu, Qiong-Jie; Yan, Wen-Guang; Wang, Lijia; Zhang, X. Peter; Tang, Yong; Organic letters 17 (2015) 4014–4017; doi:10.1021/acs.orglett.5b01909

data_1529393
_publ_section_title
;
 One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4014
_journal_page_last               4017
_journal_paper_doi               10.1021/acs.orglett.5b01909
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H24 Cl N O5'
_chemical_formula_weight         453.90
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9051(7)
_cell_length_b                   18.0332(19)
_cell_length_c                   18.2794(19)
_cell_measurement_reflns_used    4915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      48.146
_cell_measurement_theta_min      4.457
_cell_volume                     2276.2(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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16490
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.228
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
; 
 Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0035(14)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.2767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3674
_reflns_number_total             4473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01909_si_002.cif
_cod_data_source_block           dm14418
_cod_depositor_comments          'Adding full bibliography for 1529393.cif.'
_cod_database_code               1529393
_shelxl_version_number           2014-3
_shelx_res_checksum              68538
_shelx_hkl_checksum              17485