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_7135262
_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         'C23 H19 Br2 N O Se2'
_chemical_formula_sum            'C23 H19 Br2 N O Se2'
_chemical_formula_weight         643.13
_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             2025-09-09
_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                 90.366(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4802(6)
_cell_length_b                   8.4836(6)
_cell_length_c                   30.641(2)
_cell_measurement_reflns_used    4969
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0330
_cell_measurement_theta_min      3.9170
_cell_volume                     2204.3(3)
_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 0.950
_diffrn_measured_fraction_theta_max 0.719
_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    -46.00  10.00   0.50    5.30    --    1.16 -62.00  96.00  112
  2  \w      8.00  66.00   0.50    5.30    --    1.16  38.00-150.00  116
  3  \w    -25.00   1.00   0.50    5.30    --   -2.33  77.00   0.00   52
;
_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      -0.0244817000
_diffrn_orient_matrix_UB_12      -0.0541360000
_diffrn_orient_matrix_UB_13      0.0162396000
_diffrn_orient_matrix_UB_21      0.0675270000
_diffrn_orient_matrix_UB_22      -0.0470333000
_diffrn_orient_matrix_UB_23      -0.0040215000
_diffrn_orient_matrix_UB_31      0.0427278000
_diffrn_orient_matrix_UB_32      0.0431646000
_diffrn_orient_matrix_UB_33      0.0159949000
_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  0.0376
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.719
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            8272
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.719
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.444
_diffrn_reflns_theta_min         3.584
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48247
_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            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         1.060
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0444P)^2^+0.4816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3610
_reflns_number_total             4401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05556c2.cif
_cod_data_source_block           nks-mk-232-a_auto
_cod_database_code               7135262
_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   0.993
_shelx_estimated_absorpt_t_min   0.933
_diffrn_oxdiff_digest_hkl
;
01f91a5b4fe4585f55f5d9d86bde8e1114adaf
;
_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:
 C00M(H00A,H00C), C00N(H00H,H00J), C00S(H00M,H00N), C00T(H00Q,H00S)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00K(H00K), C00L(H00L), C00O(H00O), C00P(H00P), C00R(H00R)
;
_shelx_res_checksum              89846
_shelx_hkl_checksum              97986
_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 1.637
_oxdiff_exptl_absorpt_empirical_full_min 0.741