Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-<i>c</i>][1,3,5,2]oxadiazaborinine Fluorescent Dyes.
Potopnyk, Mykhaylo A.; Volyniuk, Dmytro; Luboradzki, Roman; Ceborska, Magdalena; Hladka, Iryna; Danyliv, Yan; Grazulevicius, Juozas V.; The Journal of organic chemistry 85 (2020) 6060–6072; doi:10.1021/acs.joc.0c00552

data_4038287
_publ_section_title
;
 Organolithium-Mediated Postfunctionalization of
 Thiazolo[3,2-<i>c</i>][1,3,5,2]oxadiazaborinine Fluorescent Dyes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6060
_journal_page_last               6072
_journal_paper_doi               10.1021/acs.joc.0c00552
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C18 H16 B F2 N3 O3 S2'
_chemical_formula_weight         435.27
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 110.0670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.87160(10)
_cell_length_b                   12.50580(10)
_cell_length_c                   17.17690(10)
_cell_measurement_reflns_used    21053
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.0120
_cell_measurement_theta_min      4.3100
_cell_volume                     3807.73(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, 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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0105
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33583
_diffrn_reflns_theta_full        70.06
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         4.33
_exptl_absorpt_coefficient_mu    2.949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+4.4338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                3511
_reflns_number_total             3607
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo0c00552_si_002.cif
_cod_data_source_block           2j
_cod_depositor_comments
'Adding full bibliography for 4038285--4038289.cif.'
_cod_original_cell_volume        3807.72(4)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4038287