Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.
Zhao, Ning; Xuan, Sunting; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M Graça H; The Journal of organic chemistry 80 (2015) 8377–8383; doi:10.1021/acs.joc.5b01147

data_4036241
_publ_section_title
;
 Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective
 Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8377
_journal_page_last               8383
_journal_paper_doi               10.1021/acs.joc.5b01147
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C9 H2 B Cl5 F2 N2'
_chemical_formula_sum            'C9 H2 B Cl5 F2 N2'
_chemical_formula_weight         364.19
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                100.657(3)
_cell_angle_beta                 94.187(2)
_cell_angle_gamma                94.041(2)
_cell_formula_units_Z            4
_cell_length_a                   9.4931(4)
_cell_length_b                   9.6953(4)
_cell_length_c                   13.8865(6)
_cell_measurement_reflns_used    8626
_cell_measurement_temperature    160.0(5)
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.37
_cell_volume                     1248.09(9)
_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      160.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33900
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    1.168
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.8204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0319P)^2^+0.2098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                5480
_reflns_number_total             7628
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b01147_si_010.cif
_cod_data_source_block           NZhao36
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               4036241