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_1574785
_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         'C13 H11 Cl N2 O2 S'
_chemical_formula_sum            'C13 H11 Cl N2 O2 S'
_chemical_formula_weight         294.75
_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   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                 92.005(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   8.5033(3)
_cell_length_b                   23.1754(7)
_cell_length_c                   20.2967(6)
_cell_measurement_reflns_used    16625
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.3440
_cell_measurement_theta_min      2.6980
_cell_volume                     3997.4(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35775
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.553
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43405
_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    1.469
_exptl_crystal_description       prism
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         9145
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+1.8099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7577
_reflns_number_total             9145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02912k2.cif
_cod_data_source_block           structure2j-moca251
_cod_depositor_comments
'Adding full bibliography for 1574783--1574790.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574785
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.778
_shelx_estimated_absorpt_t_max   0.898
_shelx_res_checksum              8025