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_7246294
_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         'C18 H11 B Cl2 N2 S'
_chemical_formula_sum            'C18 H11 B Cl2 N2 S'
_chemical_formula_weight         369.06
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-17
_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                 91.452(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5839(4)
_cell_length_b                   7.0849(3)
_cell_length_c                   18.9487(8)
_cell_measurement_reflns_used    3727
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      69.92
_cell_measurement_theta_min      3.82
_cell_volume                     1554.64(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      101.0
_diffrn_detector                 'Bruker PhotonIII detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            37138
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.087
_diffrn_reflns_theta_min         3.817
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.008
_exptl_absorpt_correction_T_max  0.753298
_exptl_absorpt_correction_T_min  0.579505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 37138 reflections, Rint = 0.0661
 (23176 with I > 3sig(I), Rint = 0.0593)
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: slow evaporation from chloroform solution'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0434P)^2^+0.5896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2581
_reflns_number_total             2992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra08319a2.cif
_cod_data_source_block           cu_8v00682_0m_4_a
_cod_database_code               7246294
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.501
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.514(3)
 0.486(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              43811
_olex2_submission_special_instructions 'No special instructions were received'