Organocatalytic asymmetric synthesis of tetrahydrocarbazoles via an inverse-electron-demand Diels–Alder reaction of 2,3-indole-dienes with enals
Gu, Bo-Qi; Yang, Wu-Lin; Wu, Shu-Xiao; Wang, Yan-Bing; Deng, Wei-Ping; Organic Chemistry Frontiers 5 (2018) 3430–; doi:10.1039/C8QO01042K

data_1554487
_publ_section_title
;
 Organocatalytic asymmetric synthesis of tetrahydrocarbazoles via an
 inverse-electron-demand Diels--Alder reaction of 2,3-indole-dienes with
 enals
;
_journal_issue                   23
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3430
_journal_paper_doi               10.1039/C8QO01042K
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C37 H31 N3 O4 S'
_chemical_formula_weight         613.71
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.2050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.6363(6)
_cell_length_b                   8.5322(3)
_cell_length_c                   15.2209(8)
_cell_measurement_reflns_used    8075
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      49.970
_cell_measurement_theta_min      5.362
_cell_volume                     1588.90(12)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23737
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.681
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
; 
 Flack x determined using 2076 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       0.028(3)
_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   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6224
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0290P)^2^+0.1718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5205
_reflns_number_total             6224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01042k2.cif
_cod_data_source_block           mo_d8v18344_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554487
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
_shelx_res_checksum              96999