Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids.
Yu, Mingfeng; Wong, Joseph K.-H.; Tang, Cyril; Turner, Peter; Todd, Matthew H.; Rutledge, Peter J.; Beilstein journal of organic chemistry 11 (2015) 37–41; doi:10.3762/bjoc.11.6

data_4030436
_publ_section_title
;
 Efficient deprotection of F-BODIPY derivatives: removal of BF2 using
 Br\/onsted acids.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              37
_journal_page_last               41
_journal_paper_doi               10.3762/bjoc.11.6
_journal_volume                  11
_journal_year                    2015
_chemical_formula_sum            'C19 H18 B F2 N3 O2'
_chemical_formula_weight         369.17
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_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                 96.413(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   30.367(3)
_cell_length_b                   11.8122(9)
_cell_length_c                   19.5189(16)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      2.7
_cell_volume                     6957.6(10)
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_collection       'APEX (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_molecular_graphics
;
  xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999)
  ORTEPII  (Johnson,C.K., 1976). 
  WinGX (Farrugia, 1999)
  shelXle (H&#x00FC;bschle,C.B., et al., 2011) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_crystal_treatment
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       \w+\f
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            72547
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS (Sheldrick, 1996)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3072
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.464
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         10615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.464
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.07P)^2^+0.8P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                8880
_reflns_number_total             10615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-11-6-S2.cif
_cod_data_source_block           mht13pt1
_cod_depositor_comments          'Adding full bibliography for 4030436.cif.'
_cod_database_code               4030436