8-Alkoxy- and 8-Aryloxy-BODIPYs: Straightforward Fluorescent Tagging of Alcohols and Phenols
Juan O. Flores-Rizo; Ixone Esnal; Carlos A. Osorio-Martínez; César F. A. Gómez-Durán; Jorge Bañuelos; Iñigo López Arbeloa; Keith H. Pannell; Alejandro J. Metta-Magaña; Eduardo Peña-Cabrera; Journal of Organic Chemistry 78 (2013) 5867–5877; doi:10.1021/jo400417h

data_4028328
_publ_section_title
;
 8-Alkoxy- and 8-Aryloxy-BODIPYs: Straightforward Fluorescent Tagging of
 Alcohols and Phenols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5867
_journal_page_last               5877
_journal_paper_doi               10.1021/jo400417h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C36 H51 B F2 N2 O'
_chemical_formula_weight         576.60
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.176(7)
_cell_length_b                   9.371(9)
_cell_length_c                   23.35(2)
_cell_measurement_reflns_used    328
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      16.26
_cell_measurement_theta_min      2.34
_cell_volume                     1570(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1274
_diffrn_reflns_av_sigmaI/netI    0.4891
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9083
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         0.87
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       Rods
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.153
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(4)
_refine_ls_extinction_coef       0.80(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.786
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.786
_refine_ls_R_factor_all          0.2527
_refine_ls_R_factor_gt           0.1269
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.3782
_reflns_number_gt                1533
_reflns_number_total             4886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400417h_si_001_1.cif
_cod_data_source_block           505ep1_0ms
_cod_database_code               4028328