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_1574784
_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         'C16 H16 N2 O4 S'
_chemical_formula_sum            'C16 H16 N2 O4 S'
_chemical_formula_weight         332.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.62600(10)
_cell_length_b                   10.8033(2)
_cell_length_c                   36.3680(7)
_cell_measurement_reflns_used    6582
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.8270
_cell_measurement_theta_min      2.3600
_cell_volume                     2996.21(9)
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0360
_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       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            11983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.064
_diffrn_reflns_theta_min         4.864
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30736
_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    1.474
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.00204(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0760P)^2^+1.7219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2464
_reflns_number_total             2844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02912k2.cif
_cod_data_source_block           structure2p-cua362
_cod_depositor_comments
'Adding full bibliography for 1574783--1574790.cif.'
_cod_database_code               1574784
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.361
_shelx_estimated_absorpt_t_max   0.901
_shelx_res_checksum              73061