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_7246295
_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_moiety         'C24 H16 N2 S'
_chemical_formula_sum            'C24 H16 N2 S'
_chemical_formula_weight         364.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-09-21 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.199(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4393(6)
_cell_length_b                   10.3703(5)
_cell_length_c                   17.1418(12)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.19
_cell_measurement_theta_min      5.40
_cell_volume                     1772.77(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex 4'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22077
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.151
_diffrn_reflns_theta_min         5.403
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0701 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8632.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0367P)^2^+1.3907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3345
_reflns_number_total             3468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra08319a2.cif
_cod_data_source_block           cu_8v00698_0m_a
_cod_database_code               7246295
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.751
_shelx_estimated_absorpt_t_min   0.668
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              56628
_olex2_submission_special_instructions 'No special instructions were received'