Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines
Vila, Carlos; Tortosa, Arturo; Blay, Gonzalo; Muñoz, M. Carmen; Pedro, José R.; New Journal of Chemistry 43 (2019) 130–; doi:10.1039/C8NJ05577G

data_7057960
_publ_section_title
;
 Organocatalytic enantioselective functionalization of indoles in the
 carbocyclic ring with cyclic imines
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              130
_journal_paper_doi               10.1039/C8NJ05577G
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H11 Cl2 N3 O4 S'
_chemical_formula_weight         400.23
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-10-28 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   23.7500(5)
_cell_length_b                   23.7500(5)
_cell_length_c                   5.12390(10)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.45
_cell_measurement_theta_min      3.722
_cell_volume                     2502.99(9)
_computing_cell_refinement       'APEX3, Bruker'
_computing_data_collection       'APEX3, Bruker'
_computing_data_reduction        'APEX3, Bruker'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker S8 x-ray diffraction'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            52942
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.445
_diffrn_reflns_theta_min         2.148
_exptl_absorpt_coefficient_mu    4.924
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.290
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details
;
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1160P)^2^+2.2525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3061
_reflns_number_total             3256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj05577g2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7057959--7057960.cif.'
_cod_original_cell_volume        2502.99(12)
_cod_database_code               7057960
_shelx_estimated_absorpt_t_min   0.757
_shelx_estimated_absorpt_t_max   0.827
_shelxl_version_number           2014-1
_shelx_res_checksum              52099