Synthesis and regioselective functionalization of perhalogenated BODIPYs.
Zhao, Ning; Xuan, Sunting; Byrd, Brandon; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M Graça H; Organic & biomolecular chemistry 14 (2016) 6184–6188; doi:10.1039/c6ob00935b

data_7155231
_publ_section_title
;
 Synthesis and regioselective functionalization of perhalogenated BODIPYs.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6184
_journal_page_last               6188
_journal_paper_doi               10.1039/c6ob00935b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C21 H9 B Cl4 F2 N2 S3'
_chemical_formula_sum            'C21 H9 B Cl4 F2 N2 S3'
_chemical_formula_weight         576.09
_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
_audit_update_record
;
2016-02-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                102.040(4)
_cell_angle_beta                 91.199(4)
_cell_angle_gamma                114.330(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0519(9)
_cell_length_b                   10.7177(9)
_cell_length_c                   11.8528(10)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      33.18
_cell_measurement_theta_min      3.02
_cell_volume                     1129.73(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36429
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.19
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_correction_T_min  0.7965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         8575
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.8625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                7372
_reflns_number_total             8575
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c6ob00935b2.cif
_cod_data_source_block           4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               7155231