Multi-component synthesis of 3-substituted indoles and their cyclisation to α-carbolines via I<sub>2</sub>-promoted intramolecular C2 oxidative amination/aromatisation at room temperature.
Deka, Bhaskar; Baruah, Pranjal K.; Deb, Mohit L.; Organic & biomolecular chemistry 16 (2018) 7806–7810; doi:10.1039/c8ob02362j

data_7156518
_publ_section_title
;
 Multi-component synthesis of 3-substituted indoles and their cyclisation
 to \a-carbolines via I<sub>2</sub>-promoted intramolecular C2 oxidative
 amination/aromatisation at room temperature.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7806
_journal_page_last               7810
_journal_paper_doi               10.1039/c8ob02362j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C25 H17 Br N4'
_chemical_formula_weight         453.33
_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   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-09-14 deposited with the CCDC.
2018-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7966(6)
_cell_length_b                   14.3031(12)
_cell_length_c                   18.1018(15)
_cell_measurement_reflns_used    4177
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.66
_cell_volume                     2018.6(3)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.963
_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  0.0241
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7611
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.029
_diffrn_reflns_theta_min         1.815
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_transmission_factor_max   0.764
_exptl_transmission_factor_min   0.680
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Flack x determined using 1232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                3682
_reflns_number_total             4971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02362j2.cif
_cod_data_source_block           BD_501_0m
_cod_depositor_comments
'Adding full bibliography for 7156517--7156518.cif.'
_cod_database_code               7156518
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.672
_shelx_estimated_absorpt_t_max   0.776
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_shelx_res_checksum              78471