Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed oxidative dimerization of 2-aryl indoles and cross-addition with indoles
Singh, Anoop; Vanaparthi, Satheeshvarma; Choudhary, Sachin; Krishnan, Rangan; Kumar, Indresh; RSC Advances 9 (2019) 24050–; doi:10.1039/C9RA04741G

data_7233316
_publ_section_title
;
 Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed
 oxidative dimerization of 2-aryl indoles and cross-addition with indoles
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              24050
_journal_paper_doi               10.1039/C9RA04741G
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C H Cl3, 2(C30 H24 N2 O)'
_chemical_formula_sum            'C61 H49 Cl3 N4 O2'
_chemical_formula_weight         976.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-27 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                110.2300(10)
_cell_angle_beta                 91.2620(10)
_cell_angle_gamma                108.1490(10)
_cell_formula_units_Z            2
_cell_length_a                   13.13930(10)
_cell_length_b                   14.65600(10)
_cell_length_c                   15.47680(10)
_cell_measurement_reflns_used    21326
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      74.0030
_cell_measurement_theta_min      3.5770
_cell_volume                     2629.10(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.960
_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    -25.00  18.00   0.50    5.00    --    0.00 -37.00  60.00   86
  2  \w    -28.00  76.00   0.50    5.00    --    0.00  77.00 -60.00  208
  3  \w    -71.00 -16.00   0.50    5.00    --    0.00 -37.00-150.00  110
  4  \w    -56.00 -28.00   0.50    5.00    --    0.00 -37.00  60.00   56
  5  \w    -87.00 -59.00   0.50    5.00    --    0.00 -19.00 -60.00   56
  6  \w    -49.00  22.00   0.50    5.00    --    0.00 -19.00 -60.00  142
  7  \w     43.00  83.00   0.50    6.00    --   95.80 -82.00-180.00   80
  8  \w    125.00 185.00   0.50    6.00    --   95.80  30.00 120.00  120
  9  \w     23.00 123.00   0.50    6.00    --   95.80 -15.00  60.00  200
 10  \w     12.00 125.00   0.50    6.00    --   95.80 -82.00 -90.00  226
 11  \w     76.00 105.00   0.50    6.00    --   95.80  30.00  30.00   58
 12  \w    128.00 176.00   0.50    6.00    --   95.80  30.00  30.00   96
 13  \w      6.00  37.00   0.50    6.00    --   95.80 -61.00  30.00   62
 14  \w     47.00  73.00   0.50    6.00    --   95.80 -61.00  30.00   52
 15  \w     14.00 101.00   0.50    6.00    --   95.80 -61.00 -90.00  174
 16  \w     80.00 119.00   0.50    6.00    --   95.80  30.00 120.00   78
 17  \w     49.00 119.00   0.50    6.00    --   95.80 -82.00 120.00  140
 18  \w     16.00  46.00   0.50    6.00    --   95.80 -82.00 120.00   60
 19  \w     94.00 119.00   0.50    6.00    --   95.80 -82.00-180.00   50
 20  \w     35.00  88.00   0.50    6.00    --   95.80 -30.00 120.00  106
 21  \w     92.00 126.00   0.50    6.00    --   95.80 -82.00 -30.00   68
 22  \w     42.00 116.00   0.50    6.00    --   95.80 -45.00   0.00  148
 23  \w     83.00 108.00   0.50    6.00    --   95.80 -82.00  60.00   50
 24  \w      8.00  51.00   0.50    6.00    --   95.80 -45.00-150.00   86
 25  \w     79.00 104.00   0.50    6.00    --   95.80 -82.00 -60.00   50
 26  \w     75.00 114.00   0.50    6.00    --   95.80 -82.00 150.00   78
 27  \w     12.00 128.00   0.50    6.00    --   95.80 -82.00  30.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1081285000
_diffrn_orient_matrix_UB_12      0.0877288000
_diffrn_orient_matrix_UB_13      0.0473665000
_diffrn_orient_matrix_UB_21      0.0344834000
_diffrn_orient_matrix_UB_22      -0.0708017000
_diffrn_orient_matrix_UB_23      0.0394377000
_diffrn_orient_matrix_UB_31      0.0516982000
_diffrn_orient_matrix_UB_32      -0.0385050000
_diffrn_orient_matrix_UB_33      -0.0877396000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28497
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.520
_diffrn_reflns_theta_min         3.578
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       Block
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         10338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0623
_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^)+(0.1038P)^2^+2.7287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1847
_refine_ls_wR_factor_ref         0.1867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9593
_reflns_number_total             10338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra04741g2.cif
_cod_data_source_block           exp_255-ind8a
_cod_database_code               7233316
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N1'(H1'), N2'(H2'), C14(H14), C29(H29), C13(H13), C10(H10),
 C6'(H6'), C25'(H25'), C10'(H10'), C3'(H3'), C14'(H14'), C0AA(H0AA), C11(H11),
 C26'(H26'), C18(H18), C29'(H29'), C25(H25), C3(H3), C4'(H4'), C5'(H5'),
 C22'(H22'), C11'(H11'), C19(H19), C28(H28), C13'(H13'), C6(H6), C21(H21),
 C20(H20), C26(H26), C19'(H19'), C21'(H21'), C4(H4), C5(H5), C20'(H20')
2.c Idealised Me refined as rotating group:
 C15(H15D,H15E,H15F), C30'(H30A,H30B,H30C), C15'(H15A,H15B,H15C), C30(H30D,
 H30E,H30F)
;
_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 1.675
_oxdiff_exptl_absorpt_empirical_full_min 0.747