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_4024906
_publ_section_title
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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 H11 B F2 N2 O2'
_chemical_formula_sum            'C16 H11 B F2 N2 O2'
_chemical_formula_weight         312.08
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 95.028(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2069(6)
_cell_length_b                   13.5133(11)
_cell_length_c                   15.0135(12)
_cell_measurement_reflns_used    2541
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.03
_cell_volume                     1456.5(2)
_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 4.55
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area'
_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  0.0659
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7239
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            'orange red'
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0404P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                1280
_reflns_number_total             2541
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901149y_si_002.cif
_cod_data_source_block           w
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4024906