Ru(ii)-catalyzed regioselective (3 + 2)-annulation of anilines with allenes to access 2-vinylindoles.
Dash, Om Prakash; Singh, Anurag; Shukla, Rahul K.; Volla, Chandra M. R.; Chemical science 17 (2026) 5944–5952; doi:10.1039/d5sc06303e

data_1576952
_publ_section_title
;
 Ru(ii)-catalyzed regioselective (3 + 2)-annulation of anilines with
 allenes to access 2-vinylindoles.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              5944
_journal_page_last               5952
_journal_paper_doi               10.1039/d5sc06303e
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C30 H25 N5'
_chemical_formula_sum            'C30 H25 N5'
_chemical_formula_weight         455.55
_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             2024-06-18
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-05-08 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                89.340(6)
_cell_angle_beta                 80.584(6)
_cell_angle_gamma                77.853(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9808(5)
_cell_length_b                   11.7665(9)
_cell_length_c                   13.3819(10)
_cell_measurement_reflns_used    2490
_cell_measurement_temperature    226(30)
_cell_measurement_theta_max      32.1560
_cell_measurement_theta_min      2.2780
_cell_volume                     1211.61(15)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      226(30)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -349.73  10.27   1.00    4.00   9.42 -12.98 -31.50    --   360
  2  \w    -65.46  -0.46   1.00    4.00    --  -16.01  94.56 145.16   65
  3  \w    -68.91   0.09   1.00    4.00    --  -19.47  94.56 -34.84   69
  4  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25  20.08  124
  5  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25 173.08  124
  6  \w    -65.46  -0.46   1.00    4.00    --  -16.01  94.56  73.16   65
  7  \w    -65.46  -0.46   1.00    4.00    --  -16.01  94.56   1.16   65
  8  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25 -84.92  124
  9  \f   -339.92  20.08   1.00    4.00  16.12 -12.98 -59.25    --   360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0223277000
_diffrn_orient_matrix_UB_12      0.0472651000
_diffrn_orient_matrix_UB_13      -0.0287172000
_diffrn_orient_matrix_UB_21      -0.0438870000
_diffrn_orient_matrix_UB_22      -0.0142313000
_diffrn_orient_matrix_UB_23      -0.0385806000
_diffrn_orient_matrix_UB_31      -0.0779178000
_diffrn_orient_matrix_UB_32      0.0369838000
_diffrn_orient_matrix_UB_33      0.0239841000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1595
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.771
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.0765
_exptl_crystal_size_mid          0.0657
_exptl_crystal_size_min          0.0345
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0726P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2359
_reflns_number_total             4261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06303e2.cif
_cod_data_source_block           cmrv_op_dapph_autored
_cod_depositor_comments
'Adding full bibliography for 1576951--1576952.cif.'
_cod_database_code               1576952
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N004(H004), C007(H007), C009(H009), C00A(H00A), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00P(H00P), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
2.b Idealised Me refined as rotating group:
 C00X(H00B,H00C,H00D), C00Y(H00E,H00F,H00G), C00Z(H00M,H00O,H00Q)
;
_shelx_res_checksum              59870
_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 2.796
_oxdiff_exptl_absorpt_empirical_full_min 0.480