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_4034374
_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            'C16 H13 B Br F2 N3 O S'
_chemical_formula_weight         424.07
_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-2018/1
_audit_update_record
;
2018-04-04 deposited with the CCDC.
2018-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                81.503(3)
_cell_angle_beta                 75.608(3)
_cell_angle_gamma                76.458(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4750(2)
_cell_length_b                   8.3821(3)
_cell_length_c                   13.9171(5)
_cell_measurement_reflns_used    3260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.7682
_cell_measurement_theta_min      3.2907
_cell_volume                     817.42(5)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5375
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         69.894
_diffrn_reflns_theta_min         3.293
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.912
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_correction_T_min  0.4112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0364P)^2^+0.2466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2738
_reflns_number_total             3001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00566_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4034374
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.411
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              36531
_shelx_hkl_checksum              75893