Application of the Suzuki-Miyaura Reaction for the Postfunctionalization of the Benzo[4,5]thiazolo[3,2- c][1,3,5,2]oxadiazaborinine Core: An Approach toward Fluorescent Dyes.
Potopnyk, Mykhaylo A.; Volyniuk, Dmytro; Luboradzki, Roman; Ceborska, Magdalena; Hladka, Iryna; Danyliv, Yan; Gražulevičius, Juozas Vidas; The Journal of organic chemistry 84 (2019) 5614–5626; doi:10.1021/acs.joc.9b00566

data_4034378
_publ_section_title
;
 Application of the Suzuki-Miyaura Reaction for the Postfunctionalization
 of the Benzo[4,5]thiazolo[3,2- c][1,3,5,2]oxadiazaborinine Core: An
 Approach toward Fluorescent Dyes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5614
_journal_page_last               5626
_journal_paper_doi               10.1021/acs.joc.9b00566
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C20 H16 B F2 N3 O S2'
_chemical_formula_weight         427.29
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4633(2)
_cell_length_b                   7.9239(4)
_cell_length_c                   42.334(2)
_cell_measurement_reflns_used    4085
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      69.9660
_cell_measurement_theta_min      4.1780
_cell_volume                     1832.67(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            8140
_diffrn_reflns_theta_full        69.95
_diffrn_reflns_theta_max         69.95
_diffrn_reflns_theta_min         4.18
_exptl_absorpt_coefficient_mu    2.970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+3.1125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                3110
_reflns_number_total             3234
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo9b00566_si_008.cif
_cod_data_source_block           mpc_507_02
_cod_original_cell_volume        1832.65(14)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4034378