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_4038285
_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            'C12 H11 B F2 I N3 O S'
_chemical_formula_weight         421.01
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.888(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7049(5)
_cell_length_b                   12.0661(5)
_cell_length_c                   7.7020(3)
_cell_measurement_reflns_used    2972
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.5050
_cell_measurement_theta_min      3.1290
_cell_volume                     1454.20(10)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6716
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.075
_diffrn_reflns_theta_min         2.603
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39319
_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    1.923
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.492
_refine_diff_density_min         -1.617
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0719P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3102
_reflns_number_total             3707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00552_si_002.cif
_cod_data_source_block           2c
_cod_depositor_comments
'Adding full bibliography for 4038285--4038289.cif.'
_cod_original_cell_volume        1454.19(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038285
_oxdiff_exptl_absorpt_empirical_full_min 0.631
_oxdiff_exptl_absorpt_empirical_full_max 2.174
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
_shelx_res_checksum              37095
_shelx_hkl_checksum              67415