Carboxyl BODIPY Dyes from Bicarboxylic Anhydrides: One-Pot Preparation, Spectral Properties, Photostability, and Biolabeling
Dongchuan Wang; Jiangli Fan; Xinqin Gao; Bingshuai Wang; Shiguo Sun; Xiaojun Peng; Journal of Organic Chemistry 74 (2009) 7675–7683; doi:10.1021/jo901149y

data_4024905
_publ_section_title
;
Carboxyl BODIPY Dyes from Bicarboxylic Anhydrides: One-Pot Preparation,
Spectral Properties, Photostability, and Biolabeling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7675
_journal_page_last               7683
_journal_paper_doi               10.1021/jo901149y
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C16 H14 B F2 N3 O4'
_chemical_formula_sum            'C16 H14 B F2 N3 O4'
_chemical_formula_weight         361.11
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.016(9)
_cell_angle_beta                 89.595(8)
_cell_angle_gamma                83.854(9)
_cell_formula_units_Z            2
_cell_length_a                   6.614(4)
_cell_length_b                   9.211(6)
_cell_length_c                   13.474(9)
_cell_measurement_reflns_used    4761
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      2.67
_cell_volume                     816.0(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 11.05
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3755
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slice
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.036(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0854P)^2^+0.3906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                2056
_reflns_number_total             2707
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901149y_si_001.cif
_cod_data_source_block           d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               4024905