Gold/silver-catalyzed synthesis of functionalized indoles from <i>N</i>-allyl-2-alkynylanilines and α-diazo compounds <i>via</i> 1,3-allyl migration.
Thakur, Deepika; Meena, Shivam A.; Sharma, Manvi; Verma, Akhilesh K.; Chemical communications (Cambridge, England) 61 (2025) 5313–5316; doi:10.1039/d5cc00461f

data_7134298
_publ_section_title
;
 Gold/silver-catalyzed synthesis of functionalized indoles from
 <i>N</i>-allyl-2-alkynylanilines and &#x3b1;-diazo compounds <i>via</i>
 1,3-allyl migration.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5313
_journal_page_last               5316
_journal_paper_doi               10.1039/d5cc00461f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C21 H20 Br N O2'
_chemical_formula_sum            'C21 H20 Br N O2'
_chemical_formula_weight         398.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-18 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.833(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9741(2)
_cell_length_b                   18.6365(4)
_cell_length_c                   11.5094(3)
_cell_measurement_reflns_used    16900
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.1300
_cell_measurement_theta_min      3.1970
_cell_volume                     1869.07(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -23.00  27.00   0.50    0.86    --   -5.21 -99.00 150.00  100
  2  \w    -78.00   8.00   0.50    0.86    --   -5.21 -38.00  60.00  172
  3  \w    -23.00  38.00   0.50    0.86    --    5.37 -99.00  30.00  122
  4  \w    -67.00  -1.00   0.50    0.86    --    5.37 -38.00  90.00  132
  5  \w    -23.00  27.00   0.50    0.86    --   -5.21 -99.00 -60.00  100
  6  \w    -67.00  19.00   0.50    0.86    --    5.37 -38.00 -90.00  172
  7  \w    -67.00  19.00   0.50    0.86    --    5.37 -38.00-150.00  172
  8  \w    -23.00  38.00   0.50    0.86    --    5.37 -99.00-180.00  122
  9  \w     -8.00  78.00   0.50    0.86    --    5.37  38.00  30.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0715286000
_diffrn_orient_matrix_UB_12      0.0030225000
_diffrn_orient_matrix_UB_13      -0.0423606000
_diffrn_orient_matrix_UB_21      0.0379848000
_diffrn_orient_matrix_UB_22      -0.0025541000
_diffrn_orient_matrix_UB_23      -0.0472806000
_diffrn_orient_matrix_UB_31      -0.0082289000
_diffrn_orient_matrix_UB_32      -0.0378428000
_diffrn_orient_matrix_UB_33      -0.0001898000
_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  0.0504
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38251
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.201
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0182P)^2^+1.5837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3458
_reflns_number_total             3823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00461f2.cif
_cod_data_source_block           dtr-384_auto
_cod_depositor_comments
'Adding full bibliography for 7134298--7134300.cif.'
_cod_database_code               7134298
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     25-04-2023
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H00K of C00J, H00A of C00A, H00H of C00H, H00O of C00M,
  H00L of C00K, H00E of C00D, H00D of C00C, H00Q of C00O, H00P of C00N
 At 1.5 times of:
  All C(H,H,H) groups, H00I of C00I
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00F(H00F,H00G), C00L(H00M,H00N)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00D), C00D(H00E), C00H(H00H), C00J(H00K), C00K(H00L),
 C00M(H00O), C00N(H00P), C00O(H00Q)
2.c Idealised Me refined as rotating group:
 C00P(H00R,H00S,H00T)
2.d Idealised tetrahedral OH refined as rotating group:
 C00I(H00I)
;
_shelx_res_checksum              9715
_shelx_hkl_checksum              97604
_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 4.232
_oxdiff_exptl_absorpt_empirical_full_min 0.605