Base-promoted, CBr<sub>4</sub>-mediated tandem bromination/intramolecular Friedel-Crafts alkylation of N-aryl enamines: a facile access to 1H- and 3H-indoles.
Zhao, Lan; Qiu, Changfu; Zhao, Lixin; Yin, Guangwei; Li, Fangyi; Wang, Chunhua; Li, Zheng; Organic & biomolecular chemistry 19 (2021) 5377–5382; doi:10.1039/d1ob00731a

data_7158099
_publ_section_title
;
 Base-promoted, CBr<sub>4</sub>-mediated tandem bromination/intramolecular
 Friedel-Crafts alkylation of N-aryl enamines: a facile access to 1H- and
 3H-indoles.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5377
_journal_page_last               5382
_journal_paper_doi               10.1039/d1ob00731a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H18 Br N O2'
_chemical_formula_sum            'C19 H18 Br N O2'
_chemical_formula_weight         372.25
_chemical_name_systematic
'Ethyl 6-bromo-4,7-dimethyl-2-phenyl-1H-indole-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-05-24 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.5451(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1783(2)
_cell_length_b                   7.56305(18)
_cell_length_c                   17.6627(3)
_cell_measurement_reflns_used    3677
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      76.0030
_cell_measurement_theta_min      3.6050
_cell_volume                     1626.75(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -49.00  22.00   0.50    2.28    --  -47.00  24.00  52.00  142
  2  \w     34.00 121.00   0.50    2.28    --   47.00  24.00  52.00  174
  3  \w    106.00 177.00   0.50    9.10    --  107.61  24.00  52.00  142
  4  \w     93.00 178.00   0.50    9.10    --  107.61  19.00 120.00  170
  5  \w     74.00 122.00   0.50    9.10    --  107.61 -24.00-111.00   96
  6  \w     64.00 106.00   0.50    9.10    --  107.61 -99.00   0.00   84
  7  \w     46.00  85.00   0.50    9.10    --  107.61 -99.00  30.00   78
  8  \w     36.00 108.00   0.50    9.10    --  107.61 -99.00-120.00  144
  9  \w     -7.00  18.00   0.50    2.28    --   47.00 -24.00-111.00   50
 10  \w    -89.00 -35.00   0.50    2.28    --  -47.00 125.00 120.00  108
 11  \w   -101.00 -27.00   0.50    9.10    -- -100.00 125.00 150.00  148
 12  \w    -80.00 -54.00   0.50    9.10    -- -100.00  24.00  52.00   52
 13  \w   -117.00 -33.00   0.50    2.28    --  -47.00 -24.00-111.00  168
 14  \w   -131.00 -86.00   0.50    9.10    -- -100.00 -24.00-111.00   90
 15  \w    -61.00 -33.00   0.50    9.10    -- -100.00 125.00 -90.00   56
 16  \w    -99.00 -73.00   0.50    9.10    -- -100.00 125.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0738818000
_diffrn_orient_matrix_UB_12      -0.0567663000
_diffrn_orient_matrix_UB_13      0.0660268000
_diffrn_orient_matrix_UB_21      0.0956473000
_diffrn_orient_matrix_UB_22      0.0317398000
_diffrn_orient_matrix_UB_23      0.0560680000
_diffrn_orient_matrix_UB_31      -0.0373388000
_diffrn_orient_matrix_UB_32      0.1930829000
_diffrn_orient_matrix_UB_33      0.0101459000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9497
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.360
_diffrn_reflns_theta_min         3.630
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.516
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.019
_refine_diff_density_min         -1.297
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0641
_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^)+(0.1273P)^2^+0.4850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2463
_reflns_number_total             3234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00731a2.cif
_cod_data_source_block           lfy_100k_32
_cod_depositor_comments          'Adding full bibliography for 7158099.cif.'
_cod_original_cell_volume        1626.75(6)
_cod_database_code               7158099
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.844
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C6(H6), C12(H12), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              88423
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.395
_oxdiff_exptl_absorpt_empirical_full_min 0.467