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_7134299
_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 H19 Br F N O2'
_chemical_formula_sum            'C21 H19 Br F N O2'
_chemical_formula_weight         416.28
_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             2024-01-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-24 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.989(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0327(5)
_cell_length_b                   19.2302(12)
_cell_length_c                   11.7338(7)
_cell_measurement_reflns_used    4417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7820
_cell_measurement_theta_min      3.3240
_cell_volume                     1977.7(2)
_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_temperature      293(2)
_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     -6.00  69.00   0.50    4.00    --    5.54  38.00 120.00  150
  2  \w     -3.00  24.00   0.50    4.00    --    5.54 -99.00  30.00   54
  3  \w    -11.00  15.00   0.50    4.00    --   -5.23 -99.00   0.00   52
  4  \w    -76.00   2.00   0.50    4.00    --   -5.23 -38.00-150.00  156
;
_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      -0.0315814000
_diffrn_orient_matrix_UB_12      -0.0183451000
_diffrn_orient_matrix_UB_13      -0.0526315000
_diffrn_orient_matrix_UB_21      -0.0218974000
_diffrn_orient_matrix_UB_22      0.0319602000
_diffrn_orient_matrix_UB_23      -0.0295626000
_diffrn_orient_matrix_UB_31      0.0712299000
_diffrn_orient_matrix_UB_32      0.0016725000
_diffrn_orient_matrix_UB_33      -0.0153265000
_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  0.0346
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12933
_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         26.372
_diffrn_reflns_theta_min         3.258
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82376
_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    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0325P)^2^+0.7828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3080
_reflns_number_total             4036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00461f2.cif
_cod_data_source_block           dtr-432_auto
_cod_depositor_comments
'Adding full bibliography for 7134298--7134300.cif.'
_cod_database_code               7134299
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O Br F '
_chemical_oxdiff_usercomment     11-07-2023
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00B), C00H(H00C,H00G), C00P(H00O,H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K),
 C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00Q(H00Q,H00R,H00S)
;
_shelx_res_checksum              42911
_shelx_hkl_checksum              49766
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.813