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_4036239
_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         'C30 H23 B Cl2 F2 N2 O3'
_chemical_formula_sum            'C30 H23 B Cl2 F2 N2 O3'
_chemical_formula_weight         579.21
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 94.028(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.191(2)
_cell_length_b                   17.593(3)
_cell_length_c                   22.536(5)
_cell_measurement_reflns_used    9778
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      2.546
_cell_volume                     5217.0(17)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Nonius KappaCCD '
_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  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18457
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         9573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0576P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                5460
_reflns_number_total             9573
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b01147_si_005.cif
_cod_data_source_block           NZhao45
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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_H-M      'P 21/n        '
_cod_database_code               4036239