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_7135265
_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         '0.2(C17 H17 N O S)'
_chemical_formula_sum            'C3.4 H3.4 N0.2 O0.2 S0.2'
_chemical_formula_weight         56.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-01
_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                76.164(6)
_cell_angle_beta                 68.361(6)
_cell_angle_gamma                71.046(7)
_cell_formula_units_Z            10
_cell_length_a                   7.9290(6)
_cell_length_b                   9.6466(7)
_cell_length_c                   10.3599(7)
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.6020
_cell_measurement_theta_min      4.0830
_cell_volume                     690.17(9)
_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 0.994
_diffrn_measured_fraction_theta_max 0.790
_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     -3.00  43.00   0.50    0.70    --    1.16-114.00  97.00   92
  2  \w    -10.00  64.00   0.50    0.70    --    1.16  57.00-120.00  148
  3  \w    -42.00  24.00   0.50    0.70    --    1.16 -77.00 120.00  132
  4  \w    -15.00  36.00   0.50    0.70    --    1.16 -99.00 -90.00  102
  5  \w    -15.00  33.00   0.50    0.70    --   -2.33 -99.00  60.00   96
  6  \w     -6.00  64.00   0.50    0.70    --   -2.33  38.00  60.00  140
  7  \w     -4.00  71.00   0.50    0.70    --    1.16  19.00 120.00  150
  8  \w    -42.00 -17.00   0.50    0.70    --    1.16 -77.00 -60.00   50
  9  \w     -8.00  67.00   0.50    0.70    --   -2.33  19.00 -30.00  150
;
_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      0.0200784000
_diffrn_orient_matrix_UB_12      -0.0491538000
_diffrn_orient_matrix_UB_13      0.0585826000
_diffrn_orient_matrix_UB_21      0.0910049000
_diffrn_orient_matrix_UB_22      -0.0320310000
_diffrn_orient_matrix_UB_23      -0.0438597000
_diffrn_orient_matrix_UB_31      0.0355050000
_diffrn_orient_matrix_UB_32      0.0521110000
_diffrn_orient_matrix_UB_33      0.0130995000
_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  0.0646
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11632
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.745
_diffrn_reflns_theta_min         4.081
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58993
_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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.003(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0413P)^2^+0.2081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2501
_reflns_number_total             3110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05556c2.cif
_cod_data_source_block           nks-mk-226_auto
_cod_original_cell_volume        690.17(10)
_cod_original_formula_sum        'C3.40 H3.40 N0.20 O0.20 S0.20'
_cod_database_code               7135265
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N O S '
_chemical_oxdiff_usercomment     'yellow block'
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.995
_diffrn_oxdiff_digest_hkl
;
01054fe9bc1034a404bc3f8a56d82bf72021ef
;
_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:
 C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C13(H13), C17(H17), C16(H16), C15(H15),
 C14(H14)
;
_shelx_res_checksum              93367
_shelx_hkl_checksum              52383
_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 1.786
_oxdiff_exptl_absorpt_empirical_full_min 0.401