Concise and Efficient Synthesis of Indole-Indolone Scaffolds through MeOTf-Induced Annulation of <i>N</i>-(2-Cyanoaryl)indoles.
Zou, Song; Liu, Yu; Xi, Chanjuan; ACS omega 4 (2019) 18734–18740; doi:10.1021/acsomega.9b02679

data_4516993
_publ_section_title
;
 Concise and Efficient Synthesis of Indole-Indolone Scaffolds through
 MeOTf-Induced Annulation of <i>N</i>-(2-Cyanoaryl)indoles.
;
_journal_issue                   20
_journal_name_full               'ACS omega'
_journal_page_first              18734
_journal_page_last               18740
_journal_paper_doi               10.1021/acsomega.9b02679
_journal_volume                  4
_journal_year                    2019
_chemical_formula_moiety         'C15 H8 Br N O'
_chemical_formula_sum            'C15 H8 Br N O'
_chemical_formula_weight         298.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                78.431(4)
_cell_angle_beta                 87.969(3)
_cell_angle_gamma                62.900(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3045(3)
_cell_length_b                   7.6279(4)
_cell_length_c                   11.8666(4)
_cell_measurement_reflns_used    4256
_cell_measurement_temperature    109.99(10)
_cell_measurement_theta_max      74.1760
_cell_measurement_theta_min      3.7870
_cell_volume                     575.45(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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      109.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_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    -84.00   6.00   0.50    0.05    --  -47.20 105.00 -30.00  180
  2  \w      0.00  84.00   0.50    0.05    --   47.20-105.00-130.00  168
  3  \w   -111.00 -26.00   0.50    0.05    --  -99.00 105.00 -30.00  170
  4  \w   -158.00 -81.00   0.50    0.05    --  -99.00-105.00-130.00  154
  5  \w     77.00 108.00   0.50    0.05    --  103.25-105.00-130.00   62
  6  \w     42.00  75.00   0.50    0.05    --  103.25-105.00-130.00   66
  7  \w   -114.00 -76.00   0.50    0.05    --  -47.20-125.00  60.00   76
  8  \w   -118.00 -72.00   0.50    0.05    --  -47.20-125.00  30.00   92
  9  \w     18.00  45.00   0.50    0.05    --   47.20-125.00 120.00   54
 10  \w     50.00  95.00   0.50    0.05    --   47.20-125.00 120.00   90
 11  \w    -24.00  54.00   0.50    0.05    --   47.20 -38.00 -60.00  156
 12  \w     33.00 116.00   0.50    0.05    --   47.20  57.00 -90.00  166
 13  \w   -138.00 -92.00   0.50    0.05    --  -99.00 -45.00-120.00   92
 14  \w   -167.00-142.00   0.50    0.05    --  -99.00 -45.00-120.00   50
 15  \w   -101.00 -26.00   0.50    0.05    --  -99.00 125.00  90.00  150
 16  \w   -113.00 -40.00   0.50    0.05    --  -99.00  61.00  90.00  146
 17  \w    -66.00 -28.00   0.50    0.05    --  -99.00 125.00  60.00   76
 18  \w   -167.00 -82.00   0.50    0.05    --  -99.00 -61.00 -90.00  170
 19  \w   -146.00 -89.00   0.50    0.05    --  -99.00 -45.00 -60.00  114
 20  \w   -116.00 -84.00   0.50    0.05    --  -99.00 125.00  60.00   64
 21  \w     31.00 125.00   0.50    0.05    --  103.25 -77.00-150.00  188
 22  \w     34.00 116.00   0.50    0.05    --  103.25 -45.00  30.00  164
 23  \w    139.00 165.00   0.50    0.05    --  103.25  77.00 -60.00   52
 24  \w     71.00 126.00   0.50    0.05    --  103.25 -77.00 -60.00  110
 25  \w     31.00  57.00   0.50    0.05    --  103.25 -77.00 -60.00   52
 26  \w     83.00 131.00   0.50    0.05    --  103.25  77.00 -60.00   96
 27  \w    116.00 142.00   0.50    0.05    --  103.25  45.00 -60.00   52
 28  \w     74.00 119.00   0.50    0.05    --  103.25 -61.00  90.00   90
 29  \w     96.00 129.00   0.50    0.05    --  103.25 105.00 -30.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2298847000
_diffrn_orient_matrix_UB_12      -0.0710569000
_diffrn_orient_matrix_UB_13      -0.0213483000
_diffrn_orient_matrix_UB_21      0.0437609000
_diffrn_orient_matrix_UB_22      -0.0012321000
_diffrn_orient_matrix_UB_23      0.1262789000
_diffrn_orient_matrix_UB_31      0.0399939000
_diffrn_orient_matrix_UB_32      -0.2207526000
_diffrn_orient_matrix_UB_33      0.0350822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6550
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.292
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0241
_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^)+(0.0272P)^2^+0.6029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2132
_reflns_number_total             2258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b02679_si_002.cif
_cod_data_source_block           tx801_compound_4i
_cod_database_code               4516993
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     'C H N O Br'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C2(H2), C13(H13), C8(H8), C5(H5), C3(H3), C4(H4)
;
_shelx_res_checksum              12780
_shelx_hkl_checksum              25244
_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 1.431
_oxdiff_exptl_absorpt_empirical_full_min 0.835