Access to amidines via C(sp2)–N coupling of trifluoroborate-iminiums with N-fluorobenzenesulfonimide
Knez, Damijan; Šterman, Andrej; Sosič, Izidor; Perdih, Franc; Nuñez, Gonzalo D.; Knaflič, Tilen; Arčon, Denis; Besora, Maria; Carbó, Jorge J.; Fernández, Elena; Časar, Zdenko; Chemical Science 16 (2025) 12012–12023; doi:10.1039/D5SC02912K

data_1574788
_publ_section_title
;
 Access to amidines via C(sp2)--N coupling of trifluoroborate-iminiums
 with N-fluorobenzenesulfonimide
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              12012
_journal_page_last               12023
_journal_paper_doi               10.1039/D5SC02912K
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C15 H16 N2 O3 S'
_chemical_formula_sum            'C15 H16 N2 O3 S'
_chemical_formula_weight         304.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2025-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.198(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8160(2)
_cell_length_b                   5.54900(10)
_cell_length_c                   16.7197(4)
_cell_measurement_reflns_used    6023
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.2050
_cell_measurement_theta_min      5.3020
_cell_volume                     719.43(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7568
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.072
_diffrn_reflns_theta_min         2.664
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.059(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0689P)^2^+0.1074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_full    0.715
_reflns_Friedel_fraction_max     0.708
_reflns_number_gt                2301
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02912k2.cif
_cod_data_source_block           structure2y-cua388
_cod_depositor_comments
'Adding full bibliography for 1574783--1574790.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1574788
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.364
_shelx_estimated_absorpt_t_max   0.817
_shelx_res_checksum              62894