A visible-light-mediated decarboxylative umpolung strategy to access carbamoyl/acyl fluorides in a buffer medium: expedient access to unsymmetrical ureas/amides and lysine-selective bioconjugation
Das, Subhodeep; Das, Supriyo; Rahaman, Sk Abdur; Mandal, Sourav; Jana, Ranjan; Green Chemistry 27 (2025) 13268–13280; doi:10.1039/D5GC04556H

data_1575775
_publ_section_title
;
 A visible-light-mediated decarboxylative umpolung strategy to access
 carbamoyl/acyl fluorides in a buffer medium: expedient access to
 unsymmetrical ureas/amides and lysine-selective bioconjugation
;
_journal_issue                   42
_journal_name_full               'Green Chemistry'
_journal_page_first              13268
_journal_page_last               13280
_journal_paper_doi               10.1039/D5GC04556H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '4(C9 H8 F N O)'
_chemical_formula_sum            'C36 H32 F4 N4 O4'
_chemical_formula_weight         660.65
_chemical_name_common            'indoline-1-carbonyl fluoride'
_chemical_name_systematic        'indoline-1-carbonyl fluoride'
_chemical_properties_physical    Moisture-sensitive,Photo-sensitive
_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     iterative
_audit_creation_date             2024-09-10
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-16 deposited with the CCDC.	2025-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.989(2)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   7.5098(6)
_cell_length_b                   12.5763(11)
_cell_length_c                   8.5526(7)
_cell_measurement_reflns_used    8517
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.599
_cell_measurement_theta_min      3.514
_cell_volume                     743.60(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11175
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.631
_diffrn_reflns_theta_max         66.631
_diffrn_reflns_theta_min         6.402
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1510 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.8187.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.9071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1217
_reflns_number_total             1308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04556h2.cif
_cod_data_source_block           sdd_1274_0m_a
_cod_depositor_comments          'Adding full bibliography for 1575775.cif.'
_cod_database_code               1575775
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.918
_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:
 C007(H00A,H00B), C00C(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C00A(H00C), C00B(H00D)
;
_shelx_res_checksum              31831
_shelx_hkl_checksum              14167
_olex2_submission_original_sample_id SDD-1274
_olex2_submission_special_instructions 'No special instructions were received'