Easy synthesis of imidazo[1,5-a]indol-3-ones through Rh(iii)-catalyzed C–H allenylation/annulation
Zhu, Bin; Yao, Zhenyu; Huang, Lang; Cui, Xiuling; Chemical Communications  (2021) –; doi:10.1039/D1CC04359E

data_7129153
_publ_section_title
;
 Easy synthesis of imidazo[1,5-a]indol-3-ones through Rh(iii)-catalyzed
 C--H allenylation/annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04359E
_journal_year                    2021
_chemical_formula_moiety         'C21 H19 Br N2 O2'
_chemical_formula_sum            'C21 H19 Br N2 O2'
_chemical_formula_weight         411.29
_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     iterative
_audit_creation_date             2020-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-17 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                85.011(6)
_cell_angle_beta                 73.475(6)
_cell_angle_gamma                79.776(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6120(5)
_cell_length_b                   10.8082(10)
_cell_length_c                   12.5550(7)
_cell_measurement_reflns_used    1657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.9090
_cell_measurement_theta_min      4.1350
_cell_volume                     973.81(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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   -105.00  38.00   1.00    1.00    --  -33.50   0.00-150.00  143
  2  \w    -56.00  37.00   1.00    1.00    --  -33.50  37.00  60.00   93
  3  \w     -4.00  77.00   1.00    1.00    --   36.54 -99.00 120.00   81
  4  \w    -33.00  65.00   1.00    1.00    --   36.54 -77.00-120.00   98
  5  \w    -36.00  74.00   1.00    1.00    --   36.54 -19.00  90.00  110
  6  \w     57.00 111.00   1.00    1.00    --   36.54 178.00-180.00   54
  7  \w     -4.00  77.00   1.00    1.00    --   36.54 -99.00  60.00   81
  8  \w     57.00 111.00   1.00    1.00    --   36.54 178.00  60.00   54
  9  \w     57.00 111.00   1.00    1.00    --   36.54 178.00 -30.00   54
 10  \w     57.00 111.00   1.00    1.00    --   36.54 178.00 120.00   54
 11  \w    -32.00  55.00   1.00    1.00    --   36.54 -57.00-120.00   87
 12  \w     42.00  71.00   1.00    1.00    --   36.54 -99.00-120.00   29
 13  \w     70.00  97.00   1.00    2.00    --  108.00 178.00-180.00   27
 14  \w     42.00 124.00   1.00    2.00    --  108.00 -45.00-120.00   82
 15  \w     49.00 127.00   1.00    2.00    --  108.00 -45.00  90.00   78
 16  \w    122.00 150.00   1.00    2.00    --  108.00 -15.00  30.00   28
 17  \w     44.00  71.00   1.00    2.00    --  108.00 -15.00  30.00   27
 18  \w     92.00 123.00   1.00    2.00    --  108.00 -61.00 -90.00   31
 19  \w     41.00 126.00   1.00    2.00    --  108.00 -61.00  30.00   85
 20  \w     56.00 110.00   1.00    2.00    --  108.00 -94.00 -60.00   54
 21  \w     47.00  72.00   1.00    2.00    --  108.00 -61.00   0.00   25
 22  \w     68.00 110.00   1.00    2.00    --  108.00 -94.00  30.00   42
 23  \w    137.00 177.00   1.00    2.00    --  108.00  45.00-180.00   40
 24  \w     48.00 102.00   1.00    2.00    --  108.00 -94.00-150.00   54
 25  \w     71.00 123.00   1.00    2.00    --  108.00 -45.00 150.00   52
 26  \w     38.00 112.00   1.00    2.00    --  108.00-111.00-180.00   74
 27  \w     37.00 176.00   1.00    2.00    --  108.00   0.00 -30.00  139
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1848228000
_diffrn_orient_matrix_UB_12      -0.0697123000
_diffrn_orient_matrix_UB_13      -0.0713296000
_diffrn_orient_matrix_UB_21      -0.1041578000
_diffrn_orient_matrix_UB_22      -0.0972761000
_diffrn_orient_matrix_UB_23      -0.0278216000
_diffrn_orient_matrix_UB_31      -0.0269726000
_diffrn_orient_matrix_UB_32      0.0817718000
_diffrn_orient_matrix_UB_33      -0.1026864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6968
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.675
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.010
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0406P)^2^+0.4490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             3451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04359e2.cif
_cod_data_source_block           zb319
_cod_original_cell_volume        973.80(13)
_cod_database_code               7129153
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O1Br1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.753
_shelx_estimated_absorpt_t_min   0.645
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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 1.463
_oxdiff_exptl_absorpt_empirical_full_min 0.866