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_1563275
_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_formula_moiety         'C34 H33 Cl Ir N3'
_chemical_formula_sum            'C34 H33 Cl Ir N3'
_chemical_formula_weight         711.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-12-21
_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                 102.7731(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6492(2)
_cell_length_b                   11.05361(16)
_cell_length_c                   16.4956(2)
_cell_measurement_reflns_used    5812
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      69.8560
_cell_measurement_theta_min      9.0630
_cell_volume                     2782.80(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_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  \w     26.00 110.00   1.00    1.00    --   54.00-125.00 120.00   84
  2  \w     38.00 104.00   1.00    2.00    --  108.00 -50.00  60.00   66
  3  \w     99.00 125.00   1.00    2.00    --  108.00 -38.00 -60.00   26
  4  \w     72.00 103.00   1.00    1.00    --   54.00  57.00  30.00   31
  5  \w     37.00  69.00   1.00    1.00    --    0.00  57.00  30.00   32
  6  \w     25.00 123.00   1.00    1.00    --   54.00  77.00-120.00   98
  7  \w     86.00 174.00   1.00    2.00    --  108.00  63.00-150.00   88
  8  \w     55.00  80.00   1.00    2.00    --  108.00 -38.00 -60.00   25
  9  \w     44.00 137.00   1.00    2.00    --  108.00 -77.00-120.00   93
 10  \w     42.00 125.00   1.00    2.00    --  108.00 -38.00-180.00   83
 11  \w     28.00  71.00   1.00    1.00    --   54.00  38.00-120.00   43
 12  \w     -5.00  30.00   1.00    1.00    --    0.00  57.00-180.00   35
 13  \w     37.00 145.00   1.00    2.00    --  108.00 -91.00  90.00  108
 14  \w      8.00  70.00   1.00    1.00    --   54.00 -99.00 -60.00   62
 15  \w    -20.00  29.00   1.00    1.00    --    0.00  57.00  30.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0497177000
_diffrn_orient_matrix_UB_12      -0.0750366000
_diffrn_orient_matrix_UB_13      -0.0533638000
_diffrn_orient_matrix_UB_21      0.0690319000
_diffrn_orient_matrix_UB_22      0.1011559000
_diffrn_orient_matrix_UB_23      0.0071820000
_diffrn_orient_matrix_UB_31      0.0542847000
_diffrn_orient_matrix_UB_32      -0.0597440000
_diffrn_orient_matrix_UB_33      0.0792118000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10206
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.383
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0188
_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^)+(0.0270P)^2^+0.1273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0470
_refine_ls_wR_factor_ref         0.0480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4653
_reflns_number_total             4916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02344f2.cif
_cod_data_source_block           yanzhb_1105_3
_cod_database_code               1563275
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.530
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H15(0.021) H7(0.021) H14A(0.029) H14B(0.029) H13A(0.033)
 H13B(0.033) H12A(0.026) H12B(0.026) H10A(0.032) H10B(0.032) H9A(0.045)
 H9B(0.045) H8A(0.031) H8B(0.031) H2(0.023) H3(0.028) H4(0.028) H5(0.026)
 H18(0.027) H19(0.036) H20(0.035) H21(0.029) H22(0.025) H24(0.024) H25(0.026)
 H26(0.026) H30(0.03) H31(0.034) H32(0.032) H33(0.027) H34A(0.053) H34B(0.053)
 H34C(0.053)
 Fixed X: H15(-0.147657) H7(-0.0185) H14A(-0.280893) H14B(-0.289747) H13A(-
 0.260739) H13B(-0.321425) H12A(-0.155862) H12B(-0.211054) H10A(-0.148933)
 H10B(-0.193152) H9A(-0.069905) H9B(-0.037095) H8A(0.064329) H8B(0.020818)
 H2(0.199056) H3(0.293831) H4(0.256865) H5(0.123712) H18(-0.163683) H19(-
 0.203775) H20(-0.219218) H21(-0.193614) H22(-0.14675) H24(-0.114389) H25(-
 0.155968) H26(-0.094173) H30(0.081706) H31(0.168018) H32(0.194002)
 H33(0.129495) H34A(0.000093) H34B(0.080004) H34C(-0.004114)
 Fixed Y: H15(0.668043) H7(0.815587) H14A(0.566638) H14B(0.707139)
 H13A(0.591289) H13B(0.704294) H12A(0.719974) H12B(0.831473) H10A(0.947102)
 H10B(0.876356) H9A(0.878939) H9B(0.97948) H8A(0.849455) H8B(0.743047)
 H2(0.393433) H3(0.548242) H4(0.747246) H5(0.79311) H18(0.352559) H19(0.160307)
 H20(0.123012) H21(0.275793) H22(0.464202) H24(0.530909) H25(0.526703)
 H26(0.389459) H30(0.08388) H31(-0.045211) H32(-0.001484) H33(0.16667)
 H34A(0.245711) H34B(0.217634) H34C(0.136436)
 Fixed Z: H15(0.033339) H7(0.230386) H14A(0.064504) H14B(0.047297)
 H13A(0.204414) H13B(0.175559) H12A(0.26342) H12B(0.221409) H10A(0.134355)
 H10B(0.052931) H9A(0.005651) H9B(0.07312) H8A(0.136421) H8B(0.077902)
 H2(0.353601) H3(0.40781) H4(0.375675) H5(0.286383) H18(0.200819) H19(0.147509)
 H20(0.00678) H21(-0.079861) H22(-0.0275) H24(0.315542) H25(0.441547)
 H26(0.541896) H30(0.463159) H31(0.40531) H32(0.275028) H33(0.205544)
 H34A(0.596985) H34B(0.557075) H34C(0.535647)
;
_shelx_res_checksum              4368
_shelx_hkl_checksum              98345
_olex2_date_sample_data_collection 2020-11-05
_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 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.689