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_7134300
_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         'C25 H23 N O2'
_chemical_formula_sum            'C25 H23 N O2'
_chemical_formula_weight         369.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-04-15 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.528(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4169(3)
_cell_length_b                   8.2709(2)
_cell_length_c                   20.4762(5)
_cell_measurement_reflns_used    19097
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.4340
_cell_measurement_theta_min      3.2200
_cell_volume                     1932.84(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_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      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -19.00  67.00   0.50    1.80    --   -5.53  38.00 -90.00  172
  2  \w    -78.00   8.00   0.50    1.80    --   -5.53 -38.00 -30.00  172
  3  \w    -67.00 -20.00   0.50    1.80    --    5.69 -38.00  30.00   94
  4  \w    -20.00  67.00   0.50    1.80    --   -5.53  57.00 120.00  174
  5  \w    -81.00   7.00   0.50    1.80    --   -5.53 -19.00 150.00  176
  6  \w    -78.00   9.00   0.50    1.80    --   -5.53 -57.00 120.00  174
  7  \w    -23.00  27.00   0.50    1.80    --   -5.53 -99.00  60.00  100
  8  \w    -23.00  27.00   0.50    1.80    --   -5.53 -99.00 -90.00  100
  9  \w    -23.00  27.00   0.50    1.80    --   -5.53 -99.00-150.00  100
;
_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      -0.0426680000
_diffrn_orient_matrix_UB_12      0.0383341000
_diffrn_orient_matrix_UB_13      0.0192251000
_diffrn_orient_matrix_UB_21      -0.0451684000
_diffrn_orient_matrix_UB_22      -0.0342722000
_diffrn_orient_matrix_UB_23      -0.0200560000
_diffrn_orient_matrix_UB_31      -0.0013347000
_diffrn_orient_matrix_UB_32      -0.0686146000
_diffrn_orient_matrix_UB_33      0.0207198000
_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  0.0623
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38274
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.186
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.1112
_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^)+(0.0520P)^2^+15.9612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2973
_refine_ls_wR_factor_ref         0.2989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3567
_reflns_number_total             3949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00461f2.cif
_cod_data_source_block           dtr-67-lt_auto
_cod_depositor_comments
'Adding full bibliography for 7134298--7134300.cif.'
_cod_database_code               7134300
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O'
_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:
 C00H(H00B,H00C), C00K(H00H,H00K), C00R(H00R,H00S)
2.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00S(H00T,H00U,H00V)
;
_shelx_res_checksum              76094
_shelx_hkl_checksum              25331
_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 1.733
_oxdiff_exptl_absorpt_empirical_full_min 0.660