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_1574787
_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         'C11 H10 N2 O2 S2'
_chemical_formula_sum            'C11 H10 N2 O2 S2'
_chemical_formula_weight         266.33
_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                 98.211(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5242(2)
_cell_length_b                   9.8469(2)
_cell_length_c                   10.7702(2)
_cell_measurement_reflns_used    6076
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.8860
_cell_measurement_theta_min      4.1290
_cell_volume                     1209.65(4)
_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 0.999
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8114
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.049
_diffrn_reflns_theta_min         3.875
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17643
_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    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0595P)^2^+0.7499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2082
_reflns_number_total             2295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02912k2.cif
_cod_data_source_block           structure2u-cua363
_cod_depositor_comments
'Adding full bibliography for 1574783--1574790.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574787
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.385
_shelx_estimated_absorpt_t_max   0.538
_shelx_res_checksum              23581