Pd/Brønsted acid catalysed intramolecular <i>N</i>-allylation of indoles and pyrroles with alkynes for the synthesis of N-fused heterocycles.
Bhoi, Saswat Ranjan; Debnath, Chhanda; Gandhi, Shikha; Chemical communications (Cambridge, England) 60 (2024) 428–431; doi:10.1039/d3cc05023h

data_7132444
_publ_section_title
;
 Pd/Br&#xf8;nsted acid catalysed intramolecular <i>N</i>-allylation of
 indoles and pyrroles with alkynes for the synthesis of N-fused
 heterocycles.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              428
_journal_page_last               431
_journal_paper_doi               10.1039/d3cc05023h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C24 H18 N2 O'
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40
_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             2022-10-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-29 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                66.406(8)
_cell_angle_beta                 89.765(7)
_cell_angle_gamma                84.766(6)
_cell_formula_units_Z            2
_cell_length_a                   6.3722(5)
_cell_length_b                   13.4572(11)
_cell_length_c                   14.9777(14)
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    101(1)
_cell_measurement_theta_max      31.0420
_cell_measurement_theta_min      3.5770
_cell_volume                     1171.35(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.787
_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    -18.00  30.00   0.50   17.00    --    4.97 -82.00  28.00   96
  2  \w    -31.00  11.00   0.50   17.00    --   -5.75 -82.00  28.00   84
  3  \w    -32.00   3.00   0.50   17.00    --   -5.75  82.00 149.00   70
  4  \w    -11.00  64.00   0.50   17.00    --   -5.75  19.00-180.00  150
  5  \w    -40.00  17.00   0.50   17.00    --   -5.75 -77.00-120.00  114
  6  \w    -67.00  -6.00   0.50   17.00    --   -5.75 -37.00  30.00  122
  7  \w    -15.00  13.00   0.50   17.00    --   -5.75 -99.00 150.00   56
  8  \w     -4.00  60.00   0.50   17.00    --   -5.75  37.00  30.00  128
  9  \w    -29.00  -4.00   0.50   17.00    --   -5.75  77.00  90.00   50
 10  \w    -24.00  21.00   0.50   17.00    --   -5.75  77.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0868695000
_diffrn_orient_matrix_UB_12      -0.0294557000
_diffrn_orient_matrix_UB_13      -0.0004828000
_diffrn_orient_matrix_UB_21      -0.0322775000
_diffrn_orient_matrix_UB_22      0.0011791000
_diffrn_orient_matrix_UB_23      0.0450697000
_diffrn_orient_matrix_UB_31      -0.0629124000
_diffrn_orient_matrix_UB_32      0.0498698000
_diffrn_orient_matrix_UB_33      -0.0255844000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.787
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17739
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.028
_diffrn_reflns_theta_min         3.469
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    0.993
_exptl_crystal_F_000             368
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0835P)^2^+0.2413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4536
_reflns_number_total             5903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05023h2.cif
_cod_data_source_block           sjp-sg_auto
_cod_depositor_comments          'Adding full bibliography for 7132444.cif.'
_cod_original_cell_volume        1171.36(19)
_cod_database_code               7132444
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'LIGHT YELLOW BLOCK'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C20(H20), C22(H22), C7(H7), C24(H24), C23(H23), C6(H6),
 C11(H11), C3(H3), C17(H17), C5(H5), C12(H12), C14(H14), C21(H21), C4(H4),
 C13(H13)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4181
_shelx_hkl_checksum              89158
_shelx_fab_checksum              90284
_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 1.786
_oxdiff_exptl_absorpt_empirical_full_min 0.447