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_1576951
_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         '4(C22 H15 F3 N2)'
_chemical_formula_sum            'C88 H72 F0.5 N8 O12'
_chemical_formula_weight         1443.03
_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             2022-09-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-04-29 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                94.325(2)
_cell_angle_beta                 92.658(2)
_cell_angle_gamma                90.373(2)
_cell_formula_units_Z            2
_cell_length_a                   13.1810(2)
_cell_length_b                   16.2119(4)
_cell_length_c                   16.3726(6)
_cell_measurement_reflns_used    21536
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.9280
_cell_measurement_theta_min      1.7050
_cell_volume                     3484.75(16)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_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    -10.27 349.73   1.00    2.00  77.88 -12.98  31.50    --   360
  2  \w    -68.96   0.04   1.00    2.00    --  -19.47  94.56 -34.84   69
  3  \w    -65.46  -0.46   1.00    2.00    --  -15.96  94.56 145.16   65
  4  \w   -108.63  15.37   1.00    2.00    --  -12.98 -59.25 -33.92  124
  5  \f   -349.73  10.27   1.00    2.00   9.41 -12.98 -31.50    --   360
  6  \w    -65.46  -0.46   1.00    2.00    --  -15.96  94.56   1.16   65
  7  \w   -108.63  15.37   1.00    2.00    --  -12.98 -59.25 173.08  124
  8  \w    -65.46  -0.46   1.00    2.00    --  -15.96  94.56  73.16   65
  9  \f   -339.92  20.08   1.00    2.00  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      -0.0034803000
_diffrn_orient_matrix_UB_12      -0.0309386000
_diffrn_orient_matrix_UB_13      -0.0330595000
_diffrn_orient_matrix_UB_21      0.0274147000
_diffrn_orient_matrix_UB_22      0.0259357000
_diffrn_orient_matrix_UB_23      -0.0243588000
_diffrn_orient_matrix_UB_31      0.0462452000
_diffrn_orient_matrix_UB_32      -0.0171900000
_diffrn_orient_matrix_UB_33      0.0143337000
_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  0.0962
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            139155
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.547
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             1513
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     973
_refine_ls_number_reflns         12288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0666
_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^)+(0.0619P)^2^+6.7654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1804
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9516
_reflns_number_total             12288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06303e2.cif
_cod_data_source_block           cmrv_op_220_autored
_cod_depositor_comments
'Adding full bibliography for 1576951--1576952.cif.'
_cod_original_formula_sum        'C88 H72 F0.50 N8 O12'
_cod_database_code               1576951
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOS
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 80.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     35.56
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00T(H00T), C00W(H00W), C00X(H00X), C013(H013), C014(H014),
 C015(H015), C017(H017), C018(H018), C019(H019), C01A(H01A), C01B(H01B),
 C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G), C01I(H01I), C01L(H01L),
 C01M(H01M), C01N(H01N), C01O(H01O), C01P(H01P), C01R(H01R), C01S(H01S),
 C01T(H01T), C01V(H01V), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020),
 C021(H021), C022(H022), C023(H023), C025(H025), C026(H026), C028(H028),
 C029(H029), C02A(H02A), C02B(H02B), C02C(H02C), C02D(H02D), C02E(H02E),
 C02F(H02F), C02H(H02H), C02I(H02I), C02J(H02J), C02L(H02L), C02M(H02M),
 C02N(H02N), C02O(H02O), C02P(H02P), C02Q(H02Q), C02S(H02S), C02T(H02T),
 C02V(H02V), C02W(H02W), C02X(H02X), C02Z(H02Z), C030(H030), C1(H1)
;
_shelx_res_checksum              46490
_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 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.544