On the mechanism of sp<sup>2</sup> C-H borylation using <i>ortho-N</i>-substituted pyridinium cations.
Slesarchuk, Nikita; Ma, Enlu; Miranda-Pizarro, Juan; Heikkinen, Sami; Schollmeyer, Dieter; Nieger, Martin; Vasko, Petra; Repo, Timo; Dalton transactions (Cambridge, England : 2003) 53 (2024) 9590–9595; doi:10.1039/d4dt00853g

data_7715953
_publ_section_title
;
 On the mechanism of sp<sup>2</sup> C-H borylation using
 <i>ortho-N</i>-substituted pyridinium cations.
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9590
_journal_page_last               9595
_journal_paper_doi               10.1039/d4dt00853g
_journal_volume                  53
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C11 H16 F3 N2, C24 B F20'
_chemical_formula_sum            'C35 H16 B F23 N2'
_chemical_formula_weight         912.31
_chemical_name_systematic
3-butyl-2,4,5-trifluoro-N,N-dimethylbenzenaminiumtetrakis(perfluorophenyl)borate
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-08-11 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.8363(9)
_cell_length_b                   11.7036(4)
_cell_length_c                   14.1501(4)
_cell_measurement_reflns_used    19082
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.43
_cell_volume                     3450.6(2)
_computing_cell_refinement
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area X-Red 2.3.0.0 (STOE, 2021) 
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
; 
2 runs, 159 frames, 1 deg., detector distance = 70 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans 1\%'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24592
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_min         2.428
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Absolute structure cannot be determined reliably.
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         8188
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0296P)^2^+1.4933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                6724
_reflns_number_total             8188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00853g2.cif
_cod_data_source_block           les168
_cod_depositor_comments          'Adding full bibliography for 7715953.cif.'
_cod_database_code               7715953
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              11391