Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole fluorophores
Taylor, Dominic; Malcomson, Thomas; Zhakeyev, Adilet; Rosair, Georgina M.; Paterson, Martin J.; Marques-Hueso, Jose; Dalgarno, Scott J.; Vilela, Filipe; RSC Advances 13 (2023) 5826–5832; doi:10.1039/D2RA08319A

data_7246296
_publ_section_title
;
 Regioselective electrophilic aromatic borylation as a method for
 synthesising sterically hindered benzothiadiazole fluorophores
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              5826
_journal_page_last               5832
_journal_paper_doi               10.1039/D2RA08319A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_sum            'C20 H12 N2 S3'
_chemical_formula_weight         376.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-09-21 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                89.3640(7)
_cell_angle_beta                 85.3723(7)
_cell_angle_gamma                73.5196(7)
_cell_formula_units_Z            2
_cell_length_a                   6.87730(10)
_cell_length_b                   7.41610(10)
_cell_length_c                   16.8392(3)
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.05
_cell_measurement_theta_min      5.28
_cell_volume                     820.81(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18869
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         5.271
_exptl_absorpt_coefficient_mu    4.157
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0285P)^2^+0.5143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3156
_reflns_number_total             3306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra08319a2.cif
_cod_data_source_block           cu_8v00708_0m_a
_cod_database_code               7246296
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.316
_shelx_estimated_absorpt_t_max   0.594
_shelx_res_checksum              3249