Ir(III)-catalyzed quadruple C−H activation of N-arylimidazolium and diaryliodonium salts: facile access to polysubstituted imidazo[1,2-f]phenanthridiniums
Liu, Zheng; Li, Qian; Yang, Chengyong; Zheng, Xuesong; Wu, Di; Gao, Ge; Lan, Jingbo; Chemical Communications  (2022) –; doi:10.1039/D2CC01646J

data_7130142
_publ_section_title
;
 Ir(III)-catalyzed quadruple C&#x2212;H activation of N-arylimidazolium
 and diaryliodonium salts: facile access to polysubstituted
 imidazo[1,2-f]phenanthridiniums
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01646J
_journal_year                    2022
_chemical_formula_moiety         'C24 H21 N2, H2 O, C2 F3 O2'
_chemical_formula_sum            'C26 H23 F3 N2 O3'
_chemical_formula_weight         468.46
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2022-02-18 deposited with the CCDC.	2022-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                84.081(5)
_cell_angle_beta                 83.827(5)
_cell_angle_gamma                81.200(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9876(4)
_cell_length_b                   10.9369(6)
_cell_length_c                   13.1476(7)
_cell_measurement_reflns_used    3665
_cell_measurement_temperature    297.4(3)
_cell_measurement_theta_max      71.0880
_cell_measurement_theta_min      4.0660
_cell_volume                     1124.07(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      297.4(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_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    -73.00  37.00   1.00    1.95    --  -34.85  19.00-120.00  110
  2  \w   -103.00 -16.00   1.00    1.95    --  -34.85 -57.00  60.00   87
  3  \w      1.00  75.00   1.00    1.95    --   34.85 -99.00-180.00   74
  4  \w      1.00  75.00   1.00    1.95    --   34.85 -99.00  30.00   74
  5  \w    -34.00  53.00   1.00    1.95    --   34.85 -57.00 120.00   87
  6  \w    -34.00  63.00   1.00    1.95    --   34.85 -77.00   0.00   97
  7  \w     23.00  90.00   1.00    1.95    --   34.85-125.00-180.00   67
  8  \w     16.00 103.00   1.00    1.95    --   34.85  57.00 -60.00   87
  9  \w     16.00 103.00   1.00    1.95    --   34.85  57.00 -90.00   87
 10  \w    -36.00  57.00   1.00    1.95    --   34.85 -38.00   0.00   93
 11  \w      1.00  75.00   1.00    1.95    --   34.85 -99.00 -60.00   74
 12  \w     57.00 151.00   1.00    7.79    --  106.90 178.00-180.00   94
 13  \w     37.00 110.00   1.00    7.79    --  106.90 -94.00 -90.00   73
 14  \w     35.00 133.00   1.00    7.79    --  106.90 -30.00  30.00   98
 15  \w     39.00 127.00   1.00    7.79    --  106.90 -61.00 -60.00   88
 16  \w     37.00 110.00   1.00    7.79    --  106.90 -94.00-180.00   73
 17  \w     57.00 151.00   1.00    7.79    --  106.90 178.00 150.00   94
 18  \w     87.00 175.00   1.00    7.79    --  106.90  61.00  90.00   88
 19  \w     35.00 133.00   1.00    7.79    --  106.90 -30.00 120.00   98
 20  \w     39.00 127.00   1.00    7.79    --  106.90 -61.00-180.00   88
 21  \w     87.00 175.00   1.00    7.79    --  106.90  61.00 -90.00   88
 22  \w     87.00 177.00   1.00    7.79    --  106.90  45.00   0.00   90
 23  \w     35.00 133.00   1.00    7.79    --  106.90 -30.00 -60.00   98
 24  \w     87.00 177.00   1.00    7.79    --  106.90  45.00 -60.00   90
 25  \w     36.00 113.00   1.00    7.79    --  106.90-111.00 150.00   77
 26  \w   -103.00 -16.00   1.00    1.95    --  -34.85 -57.00 150.00   87
 27  \w      6.00 104.00   1.00    1.95    --   34.85  77.00  90.00   98
 28  \w      6.00 104.00   1.00    1.95    --   34.85  77.00 150.00   98
 29  \w      6.00 104.00   1.00    1.95    --   34.85  77.00   0.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0114430000
_diffrn_orient_matrix_UB_12      -0.1176716000
_diffrn_orient_matrix_UB_13      -0.0569512000
_diffrn_orient_matrix_UB_21      0.0229761000
_diffrn_orient_matrix_UB_22      -0.0813139000
_diffrn_orient_matrix_UB_23      0.1017990000
_diffrn_orient_matrix_UB_31      -0.1943353000
_diffrn_orient_matrix_UB_32      0.0041684000
_diffrn_orient_matrix_UB_33      0.0198230000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12035
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.330
_diffrn_reflns_theta_min         4.106
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0811
_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^)+(0.1656P)^2^+0.2653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2433
_refine_ls_wR_factor_ref         0.2704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3240
_reflns_number_total             4283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01646j2.cif
_cod_data_source_block           zxs-ag2o
_cod_original_cell_volume        1124.07(11)
_cod_database_code               7130142
_reflns_odcompleteness_completeness 99.63
_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, All O(H,H) groups
2. Others
 Sof(O00Z)=1-FVAR(1)
 Sof(O00Y)=FVAR(1)
3.a Free rotating group:
 O003(H00U,H00V)
3.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
3.c Idealised Me refined as rotating group:
 C00J(H00A,H00B,H00C), C00V(H00J,H00K,H00L), C00X(H00R,H00S,H00T)
;
_shelx_res_checksum              30198
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-12
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.706
_oxdiff_exptl_absorpt_empirical_full_min 0.613