Catalytic alkoxysilylation of C–H bonds with tert-butyl-substituted alkoxysilyldiazenes
Saadi, Lamine; Valade, Loïc; Chauvier, Clément; Chemical Science 16 (2025) 9794–9801; doi:10.1039/D5SC02059J

data_1574491
_publ_section_title
;
 Catalytic alkoxysilylation of C--H bonds with tert-butyl-substituted
 alkoxysilyldiazenes
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9794
_journal_page_last               9801
_journal_paper_doi               10.1039/D5SC02059J
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C20 H22 N2 Si'
_chemical_formula_sum            'C20 H22 N2 Si'
_chemical_formula_weight         318.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-26 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 132.881(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   30.145(3)
_cell_length_b                   15.0646(13)
_cell_length_c                   21.593(3)
_cell_measurement_reflns_used    9734
_cell_measurement_temperature    200
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.3
_cell_volume                     7185.4(14)
_computing_cell_refinement       'SAINT Bruker'
_computing_data_collection       'APEX 4 bruker'
_computing_data_reduction        'SAINT Bruker'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'curved graphite monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34880
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         2.439
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Mo sealed tube'
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0486 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.9382.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       prism
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+4.5556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4986
_reflns_number_total             8964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02059j2.cif
_cod_data_source_block           las_471bis_0ma
_cod_depositor_comments
'Adding full bibliography for 1574491--1574492.cif.'
_cod_original_cell_volume        7185.6(14)
_cod_database_code               1574491
_shelx_shelxl_version_number     2017/1
_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), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C33(H33),
  C35(H35), C36(H36), C37(H37), C38(H38)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C),
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C40(H40A,H40B,
 H40C)
;
_shelx_res_checksum              74708
_olex2_submission_special_instructions 'No special instructions were received'