An Effective and Versatile Strategy for the Synthesis of Structurally Diverse Heteroarylsilanes via Ir(III)-Catalyzed C−H Silylation
Yan, Zhi-Bo; Peng, Meng; Chen, Qi-Long; Lu, Ka; Tu, Yong Qiang; Dai, Kun Long; Zhang, Fu-Min; Zhang, Xiao-Ming; Chemical Science  (2021) –; doi:10.1039/D1SC02344F

data_1563273
_publ_section_title
;
 An Effective and Versatile Strategy for the Synthesis of Structurally
 Diverse Heteroarylsilanes via Ir(III)-Catalyzed C&#x2212;H Silylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02344F
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H38 Cl Ir N4'
_chemical_formula_sum            'C36 H38 Cl Ir N4'
_chemical_formula_weight         754.35
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-08 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   26.9599(4)
_cell_length_b                   26.9599(4)
_cell_length_c                   11.3490(2)
_cell_measurement_reflns_used    15637
_cell_measurement_temperature    270.82(19)
_cell_measurement_theta_max      75.1180
_cell_measurement_theta_min      3.2590
_cell_volume                     7143.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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      270.82(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_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 -10.00   0.50    0.08    --  -43.05 102.00   7.00  126
  2  \w    -53.00 -24.00   0.50    0.30    -- -100.00  45.00  30.00   58
  3  \w    -74.00 -26.00   0.50    0.30    -- -100.00  67.00 -81.00   96
  4  \w    -55.00 -28.00   0.50    0.30    -- -100.00 125.00-120.00   54
  5  \w    -74.00 -30.00   0.50    0.30    -- -100.00  61.00 -90.00   88
  6  \w    -70.00 -44.00   0.50    0.30    -- -100.00  61.00  60.00   52
  7  \w    -98.00 -53.00   0.50    0.30    -- -100.00  74.00 122.00   90
  8  \w   -164.00 -72.00   0.50    0.30    -- -100.00 -74.00  -6.00  184
  9  \w   -115.00 -52.00   0.50    0.08    --  -43.05-179.00 -30.00  126
 10  \w     35.00  78.00   0.50    0.30    --  109.26 -77.00  60.00   86
 11  \w     35.00  97.00   0.50    0.30    --  109.26 -77.00  90.00  124
 12  \w     40.00  83.00   0.50    0.30    --  109.26 -77.00 -30.00   86
 13  \w   -100.00 -75.00   0.50    0.30    -- -100.00 125.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0271821000
_diffrn_orient_matrix_UB_12      -0.0473779000
_diffrn_orient_matrix_UB_13      0.0943148000
_diffrn_orient_matrix_UB_21      -0.0460544000
_diffrn_orient_matrix_UB_22      -0.0392890000
_diffrn_orient_matrix_UB_23      -0.0888606000
_diffrn_orient_matrix_UB_31      0.0386554000
_diffrn_orient_matrix_UB_32      -0.0237920000
_diffrn_orient_matrix_UB_33      -0.0404191000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27060
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.092
_diffrn_reflns_theta_min         5.012
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 2923 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.118(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         8514
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0663P)^2^+4.7513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.813
_reflns_Friedel_fraction_max     0.741
_reflns_number_gt                7824
_reflns_number_total             8514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02344f2.cif
_cod_data_source_block           yanzhb_1225_1
_cod_database_code               1563273
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.610
_shelx_estimated_absorpt_t_min   0.462
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H00B(0.095) H00D(0.067) H00A(0.076) H00C(0.076) H00G(0.104)
 H00H(0.109) H00I(0.088) H00J(0.089) H00L(0.091) H00M(0.097) H00E(0.094)
 H00F(0.094) H00O(0.082) H00Q(0.092) H00K(0.208) H00N(0.208) H00P(0.208)
 H00T(0.109) H00U(0.146) H00V(0.121) H00W(0.087) H00R(0.137) H00S(0.137)
 H00X(0.117) H00Y(0.117) H00Z(0.198) H(0.198) HA(0.198) H01A(0.116) H01B(0.116)
 H01C(0.123) H01D(0.123) H01E(0.153) H01F(0.153) H013(0.131) H014(0.162)
 H015(0.153) H68(0.176)
 Fixed X: H00B(0.637052) H00D(0.859847) H00A(0.761663) H00C(0.698635)
 H00G(0.62506) H00H(0.705204) H00I(0.696711) H00J(0.727313) H00L(0.794297)
 H00M(0.976142) H00E(1.036707) H00F(1.099671) H00O(0.799711) H00Q(1.030531)
 H00K(0.756178) H00N(0.813352) H00P(0.77274) H00T(0.920337) H00U(0.898491)
 H00V(0.998575) H00W(0.833415) H00R(1.046703) H00S(1.082015) H00X(1.002165)
 H00Y(0.96832) H00Z(0.857196) H(0.883739) HA(0.826578) H01A(1.117564)
 H01B(1.102574) H01C(1.008343) H01D(1.063817) H01E(1.100219) H01F(1.038945)
 H013(0.899792) H014(0.837779) H015(0.810084) H68(0.831342)
 Fixed Y: H00B(0.405264) H00D(0.489656) H00A(0.527686) H00C(0.495155)
 H00G(0.329844) H00H(0.322604) H00I(0.499949) H00J(0.500571) H00L(0.394162)
 H00M(0.441995) H00E(0.584216) H00F(0.624015) H00O(0.358148) H00Q(0.532892)
 H00K(0.456133) H00N(0.508497) H00P(0.518458) H00T(0.342867) H00U(0.646)
 H00V(0.651461) H00W(0.300389) H00R(0.636077) H00S(0.603907) H00X(0.522381)
 H00Y(0.555619) H00Z(0.449876) H(0.485266) HA(0.426277) H01A(0.631756)
 H01B(0.680746) H01C(0.700288) H01D(0.72264) H01E(0.69781) H01F(0.65732)
 H013(0.59764) H014(0.62996) H015(0.675078) H68(0.668936)
 Fixed Z: H00B(0.754086) H00D(0.410462) H00A(0.708504) H00C(0.660904)
 H00G(0.871474) H00H(0.920067) H00I(0.456446) H00J(0.27509) H00L(0.865973)
 H00M(0.475679) H00E(0.718315) H00F(0.672955) H00O(0.666471) H00Q(0.520381)
 H00K(0.077066) H00N(0.031732) H00P(0.114982) H00T(0.483178) H00U(0.469368)
 H00V(0.467822) H00W(0.590912) H00R(0.290858) H00S(0.284797) H00X(0.328121)
 H00Y(0.345868) H00Z(0.254296) H(0.138804) HA(0.132948) H01A(0.473961)
 H01B(0.454931) H01C(0.667109) H01D(0.58876) H01E(0.743958) H01F(0.797478)
 H013(0.800989) H014(0.852174) H015(0.728789) H68(0.528821)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              88397
_shelx_hkl_checksum              83763
_shelx_fab_checksum              79242
_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.705