Synthesis of N-fused polycyclic indoles via a Pd-catalyzed multicomponent cascade reaction consisting of an amide-directed [3+1+1] annulation reaction of 3-diazo oxindole and isocyanides
Soam, Pooja; Mandal, Debasish; Tyagi, Vikas; New Journal of Chemistry 48 (2024) 2639–2648; doi:10.1039/D3NJ04886A

data_7062949
_publ_section_title
;
 Synthesis of N-fused polycyclic indoles via a Pd-catalyzed multicomponent
 cascade reaction consisting of an amide-directed [3+1+1] annulation
 reaction of 3-diazo oxindole and isocyanides
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2639
_journal_page_last               2648
_journal_paper_doi               10.1039/D3NJ04886A
_journal_volume                  48
_journal_year                    2024
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C23 H32 N4 O2'
_chemical_formula_sum            'C23 H32 N4 O2'
_chemical_formula_weight         396.52
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-15
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                103.8143(19)
_cell_angle_beta                 97.5949(17)
_cell_angle_gamma                98.8737(17)
_cell_formula_units_Z            2
_cell_length_a                   9.59358(18)
_cell_length_b                   10.5593(2)
_cell_length_c                   11.9248(3)
_cell_measurement_reflns_used    8293
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7460
_cell_measurement_theta_min      3.2960
_cell_volume                     1140.90(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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    -30.00  -4.00   0.50   10.00    --   -9.79 -90.00 125.00   52
  2  \w     -7.00  30.00   0.50   10.00    --   -9.79  90.00-119.00   74
  3  \w    -19.00  32.00   0.50   10.00    --   10.07  90.00-119.00  102
  4  \w      9.00  35.00   0.50   10.00    --   10.07 -90.00 125.00   52
  5  \w    -63.00  -9.00   0.50   10.00    --   -9.79 -19.00 120.00  108
  6  \w    -79.00   2.00   0.50   10.00    --   -9.79 -19.00  30.00  162
  7  \w     -7.00  53.00   0.50   10.00    --   -9.79  38.00 -30.00  120
  8  \w    -39.00 -14.00   0.50   10.00    --   10.07 126.00   6.42   50
  9  \w    -18.00  37.00   0.50   10.00    --   10.07 -99.00  30.00  110
 10  \w    -49.00  12.00   0.50   10.00    --   10.07 -38.00-150.00  122
 11  \w     15.00  56.00   0.50   10.00    --   10.07-125.00 -30.00   82
 12  \w    -23.00   2.00   0.50   10.00    --   10.07 119.00  27.76   50
 13  \w    -19.00  39.00   0.50   10.00    --   10.07 -99.00-180.00  116
 14  \w    -19.00  41.00   0.50   10.00    --   10.07 -99.00  90.00  120
 15  \w     48.00  73.00   0.50   10.00    --   10.07  57.00  30.00   50
 16  \w      3.00  28.00   0.50   10.00    --   10.07-125.00-120.00   50
 17  \w      6.00  32.00   0.50   10.00    --   10.07  57.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0438453000
_diffrn_orient_matrix_UB_12      0.0234090000
_diffrn_orient_matrix_UB_13      0.0563240000
_diffrn_orient_matrix_UB_21      -0.0133242000
_diffrn_orient_matrix_UB_22      0.0649230000
_diffrn_orient_matrix_UB_23      0.0033900000
_diffrn_orient_matrix_UB_31      -0.0606544000
_diffrn_orient_matrix_UB_32      -0.0143974000
_diffrn_orient_matrix_UB_33      0.0262331000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15515
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.237
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0694P)^2^+0.0752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3279
_reflns_number_total             4625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04886a2.cif
_cod_data_source_block           ex-thapar-pooja
_cod_depositor_comments          'Adding full bibliography for 7062949.cif.'
_cod_original_cell_volume        1140.89(4)
_cod_database_code               7062949
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O'
_diffrn_oxdiff_ac3_digest_frames
;
01f38e5563abb6daf0f4fc1d0cf94e7a9001472566f
;
_diffrn_oxdiff_ac3_digest_hkl
;
01233bd18a618d21ba4407bf16f195df36644f
;
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2A), C5(H5), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C23(H23A,H23B,H23C), C22(H22A,H22B,
 H22C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C12(H12A,H12B,H12C), C11(H11A,
 H11B,H11C), C13(H13A,H13B,H13C)
;
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.829