Ag(I)-Mediated Mono-selective C(sp2)─H Chalcogenation of α-Aminotropones and Their Peptides at Room Temperature
Kar, Malobika; Sharma, Nagendra K.; Chemical Communications  (2025) –; doi:10.1039/D5CC05556C

data_7135263
_publ_section_title
;
 Ag(I)-Mediated Mono-selective C(sp2)&#x2500;H Chalcogenation of
 \a-Aminotropones and Their Peptides at Room Temperature
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC05556C
_journal_year                    2025
_chemical_formula_moiety         'C17 H16 Br N O Se'
_chemical_formula_sum            'C17 H16 Br N O Se'
_chemical_formula_weight         409.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-10
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-24 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.504(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9325(6)
_cell_length_b                   19.3831(15)
_cell_length_c                   10.3168(8)
_cell_measurement_reflns_used    4008
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.6930
_cell_measurement_theta_min      3.6640
_cell_volume                     1559.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.774
_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     -6.00  41.00   0.50    3.00    --    1.16-110.00  38.00   94
  2  \w    -65.00   5.00   0.50    3.00    --    1.16 -38.00-180.00  140
  3  \w    -25.00  21.00   0.50    3.00    --   -2.33  77.00 -60.00   92
  4  \w    -15.00  33.00   0.50    3.00    --   -2.33 -99.00 -90.00   96
  5  \w    -71.00  -9.00   0.50    3.00    --   -2.33 -19.00  90.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0898571000
_diffrn_orient_matrix_UB_12      -0.0023006000
_diffrn_orient_matrix_UB_13      0.0223005000
_diffrn_orient_matrix_UB_21      -0.0028007000
_diffrn_orient_matrix_UB_22      -0.0356904000
_diffrn_orient_matrix_UB_23      -0.0153467000
_diffrn_orient_matrix_UB_31      0.0137551000
_diffrn_orient_matrix_UB_32      0.0077411000
_diffrn_orient_matrix_UB_33      -0.0644707000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.774
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12746
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.772
_diffrn_reflns_theta_min         3.353
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0306P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2602
_reflns_number_total             3452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05556c2.cif
_cod_data_source_block           nks-mk-232-r_auto
_cod_database_code               7135263
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N O Se Br'
_chemical_oxdiff_usercomment     'yellow block'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.952
_diffrn_oxdiff_digest_hkl
;
01524968853900021551225892e767c0179b23
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C11(H11a,H11b), C9(H9a,H9b), C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C13(H13), C14(H14), C7(H7), C3(H3), C17(H17), C16(H16)
;
_shelx_res_checksum              13762
_shelx_hkl_checksum              13249
_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 6.047
_oxdiff_exptl_absorpt_empirical_full_min 0.395