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_1563274
_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         'C15 H23 N O Si'
_chemical_formula_sum            'C15 H23 N O Si'
_chemical_formula_weight         261.43
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.11.30 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5622)
;
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.07243(19)
_cell_length_b                   17.07243(19)
_cell_length_c                   21.9046(4)
_cell_measurement_reflns_used    6303
_cell_measurement_temperature    149.96(10)
_cell_measurement_theta_max      76.0020
_cell_measurement_theta_min      3.2820
_cell_volume                     6384.49(15)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.96(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_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    -25.00   4.00   1.00    0.15    --  -46.32  19.00 -90.00   29
  2  \w    -69.00 -44.00   1.00    0.70    -- -102.00  61.00  90.00   25
  3  \w    -69.00 -44.00   1.00    0.70    -- -102.00  61.00 120.00   25
  4  \w   -105.00 -79.00   1.00    0.70    -- -102.00   2.00  52.00   26
  5  \w   -174.00-149.00   1.00    0.70    -- -102.00   2.00  52.00   25
  6  \w    -96.00 -67.00   1.00    0.15    --  -46.32-137.00 -13.00   29
  7  \w     27.00  89.00   1.00    0.15    --   46.32-132.00 163.00   62
  8  \w    151.00 176.00   1.00    0.70    --  103.99  45.00 -30.00   25
  9  \w     92.00 175.00   1.00    0.70    --  103.99  45.00  60.00   83
 10  \w     92.00 143.00   1.00    0.70    --  103.99  45.00 -30.00   51
 11  \w     42.00 103.00   1.00    0.70    --  103.99-132.00 163.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0022570000
_diffrn_orient_matrix_UB_12      0.0280819000
_diffrn_orient_matrix_UB_13      -0.0668239000
_diffrn_orient_matrix_UB_21      -0.0016613000
_diffrn_orient_matrix_UB_22      -0.0856912000
_diffrn_orient_matrix_UB_23      -0.0219361000
_diffrn_orient_matrix_UB_31      -0.0902076000
_diffrn_orient_matrix_UB_32      0.0023644000
_diffrn_orient_matrix_UB_33      -0.0012432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9382
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.231
_diffrn_reflns_theta_min         3.282
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37532
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0762P)^2^+2.7684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2853
_reflns_number_total             3209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02344f2.cif
_cod_data_source_block           yanzhb_0120
_cod_original_cell_volume        6384.49(18)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               1563274
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.869
_diffrn_oxdiff_digest_frames
;
0135eaa85b0fc23eb8080f5303423b02ff00029e143
;
_diffrn_oxdiff_digest_hkl
;
01322a70647203d8bf3e07b78c3fff9dbee268
;
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H11A,H11B), C12(H14A,H14B), C14(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H2), C2(H4), C4(H7), C5(H6), C7(H10)
2.c Idealised Me refined as rotating group:
 C9(H12A,H12B,H12C), C11(H16A,H16B,H16C), C13(H15A,H15B,H15C), C15(H17A,H17B,
 H17C)
;
_shelx_res_checksum              27758
_shelx_hkl_checksum              32813
_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 2.247
_oxdiff_exptl_absorpt_empirical_full_min 0.383