BODIPYs α-appended with distyryl-linked aryl bisboronic acids: single-step cell staining and turn-on fluorescence binding with D-glucose.
Alkaş, Adil; Kofsky, Joshua M.; Sullivan, Em C.; Nebel, Daisy; Robertson, Katherine N.; Capicciotti, Chantelle J.; Jakeman, David L.; Johnson, Erin R.; Thompson, Alison; Organic & biomolecular chemistry 22 (2024) 7448–7459; doi:10.1039/d4ob01013b

data_7160110
_publ_section_title
;
 BODIPYs &#x3b1;-appended with distyryl-linked aryl bisboronic acids:
 single-step cell staining and turn-on fluorescence binding with
 D-glucose.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7448
_journal_page_last               7459
_journal_paper_doi               10.1039/d4ob01013b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C43 H53 B3 F2 N2 O4'
_chemical_formula_sum            'C43 H53 B3 F2 N2 O4'
_chemical_formula_weight         732.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-01-28 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.0246(8)
_cell_length_b                   11.7719(3)
_cell_length_c                   24.1756(6)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      26.3761
_cell_measurement_theta_min      2.3817
_cell_volume                     8260.2(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            98626
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_min         1.867
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             3120
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1321
_refine_ls_number_reflns         15965
_refine_ls_number_restraints     2131
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0739
_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^)+(0.0708P)^2^+5.7833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1742
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                11816
_reflns_number_total             15965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01013b2.cif
_cod_data_source_block           Compound3_AT009_AA3
_cod_depositor_comments
'Adding full bibliography for 7160107--7160111.cif.'
_cod_database_code               7160110
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.999
_diffrn_source_source            'microfocus sealed tube'
_shelx_res_checksum              84771