Silver-Catalysed Intermolecular Benzylic-Selective C–H Amidation via Nitrene Transfer
Panja, Subir; Trinh, Tuan Anh; Warrington, Ethan M.; Hu, Derek B.; Garman, Leah C.; Guzei, Ilia; Schomaker, Jennifer; Chemical Science  (2026) –; doi:10.1039/D5SC10184K

data_1576891
_publ_section_title
;
 Silver-catalysed intermolecular benzylic-selective C-H amidation
 <i>via</i> nitrene transfer.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              9264
_journal_page_last               9269
_journal_paper_doi               10.1039/d5sc10184k
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C58 H70 Ag3 F12 N8 O8 S4, C2 F6 N O4 S2'
_chemical_formula_sum            'C60 H70 Ag3 F18 N9 O12 S6'
_chemical_formula_weight         1967.22
_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     dual
_audit_creation_date             2025-09-03
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2025.09.01 svn.r6e5f9f42 for OlexSys, GUI svn.r7317)
;
_audit_update_record
;
2025-09-29 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.655(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.859(2)
_cell_length_b                   15.785(3)
_cell_length_c                   22.301(5)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.660
_cell_measurement_theta_min      2.237
_cell_volume                     3821.0(13)
_computing_cell_refinement       'SAINT+ V8.41 (Bruker AXS LLC, 1997-2024)'
_computing_data_collection       'APEX6 Ver. 2024.9-0. (Bruker AXS LLC, 2024)'
_computing_data_reduction        'SAINT+ V8.41 (Bruker AXS LLC, 1997-2024)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_crystal_treatment        'flash cooled with cold N~2~ gas'
_diffrn_detector                 '100 x 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      'Oxford Cryostream 800'
_diffrn_measurement_device       '\k-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ' \w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen mount'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON III'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            88983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.721
_diffrn_reflns_theta_min         2.063
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_type              'Incoatec I\mS Diamond II'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_max  0.4315
_exptl_absorpt_correction_T_min  0.3654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.423
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         9865
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.297
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0339P)^2^+8.3214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8692
_reflns_number_total             9865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc10184k2.cif
_cod_data_source_block           schomaker124
_cod_depositor_comments
'Adding full bibliography for 1576891--1576892.cif.'
_cod_original_cell_volume        3820.8(14)
_cod_database_code               1576891
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.922
_diffrn_measurement_specimen_attachment_type 'paratone oil'
_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. Rigid body (RIGU) restrains
 C30, F7, F8, F9, F7A, F8A, F9A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Same fragment restrains
{S3, C30, F7A, F8A, F9A} sigma for 1-2: 0.005, 1-3: 0.01
{S3, C30, F8A, F9A, F7A} sigma for 1-2: 0.005, 1-3: 0.01
{S3, C30, F7, F8, F9} sigma for 1-2: 0.005, 1-3: 0.01
{S3, C30, F8, F9, F7} sigma for 1-2: 0.005, 1-3: 0.01
as in
{S2, C29, F4, F5, F6}
4. Others
 Fixed Sof: F7(0.5) F8(0.5) F9(0.5) O5(0.5) O6(0.5) N5(0.5) F7A(0.5) F8A(0.5)
 F9A(0.5) O5A(0.5) O6A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C11(H11), C17(H17), C20(H20), C26(H26), C27(H27)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              81510
_olex2_submission_special_instructions 'No special instructions were received'