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_4516994
_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         'C16 H11 N O2'
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26
_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             2019-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                97.900(3)
_cell_angle_beta                 90.784(3)
_cell_angle_gamma                104.758(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2824(2)
_cell_length_b                   8.2333(3)
_cell_length_c                   9.9984(4)
_cell_measurement_reflns_used    4311
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      75.1490
_cell_measurement_theta_min      4.4510
_cell_volume                     573.46(4)
_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      169.99(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_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   -120.00 -35.00   0.50    0.05    --  -47.20 -41.00  30.00  170
  2  \w    -25.00  59.00   0.50    0.05    --   47.20 -41.00  30.00  168
  3  \w     35.00 120.00   0.50    0.05    --   47.20  41.00-177.00  170
  4  \w   -168.00 -87.00   0.50    0.05    --  -99.00 -41.00  30.00  162
  5  \w   -111.00 -26.00   0.50    0.05    --  -99.00  41.00-177.00  170
  6  \w     91.00 169.00   0.50    0.05    --  103.25  41.00-177.00  156
  7  \w     31.00  72.00   0.50    0.05    --  103.25 -41.00  30.00   82
  8  \w    -93.00 -14.00   0.50    0.05    --  -47.20 125.00 -60.00  158
  9  \w    -51.00 -25.00   0.50    0.05    --  -47.20  41.00-177.00   52
 10  \w   -120.00 -72.00   0.50    0.05    --  -47.20-125.00 -30.00   96
 11  \w    -24.00   2.00   0.50    0.05    --  -47.20  41.00-177.00   52
 12  \w     83.00 115.00   0.50    0.05    --   47.20  38.00-150.00   64
 13  \w   -121.00 -28.00   0.50    0.05    --  -99.00  77.00   0.00  186
 14  \w   -166.00-115.00   0.50    0.05    --  -99.00 -94.00-150.00  102
 15  \w    -76.00 -30.00   0.50    0.05    --  -99.00  77.00-120.00   92
 16  \w   -162.00 -85.00   0.50    0.05    --  -99.00 -15.00-120.00  154
 17  \w   -117.00 -80.00   0.50    0.05    --  -99.00  77.00-120.00   74
 18  \w    127.00 169.00   0.50    0.05    --  103.25  45.00 -60.00   84
 19  \w     31.00 112.00   0.50    0.05    --  103.25 -15.00   0.00  162
 20  \w     45.00 108.00   0.50    0.05    --  103.25 -94.00 120.00  126
 21  \w     39.00 104.00   0.50    0.05    --  103.25 -94.00  60.00  130
 22  \w     93.00 130.00   0.50    0.05    --  103.25  30.00 -30.00   74
 23  \w     82.00 114.00   0.50    0.05    --  103.25 -45.00-180.00   64
 24  \w     32.00 108.00   0.50    0.05    --  103.25 -45.00 120.00  152
 25  \w     77.00 107.00   0.50    0.05    --  103.25 -94.00   0.00   60
 26  \w     74.00 104.00   0.50    0.05    --  103.25 -94.00-120.00   60
 27  \w     44.00  72.00   0.50    0.05    --  103.25 -94.00   0.00   56
 28  \w     48.00  76.00   0.50    0.05    --  103.25 -45.00-180.00   56
;
_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      -0.0159165000
_diffrn_orient_matrix_UB_12      -0.1920873000
_diffrn_orient_matrix_UB_13      -0.0225739000
_diffrn_orient_matrix_UB_21      -0.1839199000
_diffrn_orient_matrix_UB_22      -0.0314418000
_diffrn_orient_matrix_UB_23      0.0778039000
_diffrn_orient_matrix_UB_31      -0.1179045000
_diffrn_orient_matrix_UB_32      -0.0191734000
_diffrn_orient_matrix_UB_33      -0.1330337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.429
_diffrn_reflns_theta_min         4.470
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92004
_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    1.444
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0584P)^2^+0.1197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2018
_reflns_number_total             2258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b02679_si_004.cif
_cod_data_source_block           tx758_compound_4u
_cod_database_code               4516994
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     'C H N '
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C10(H10), C13(H13), C2(H2), C9(H9), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              31083
_shelx_hkl_checksum              27793
_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 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.555