Flexible BODIPY Platform That Offers an Unexpected Regioselective Heterocyclization Reaction toward Preparation of 2-Pyridone[ a]-Fused BODIPYs.
Didukh, Natalia O.; Yakubovskyi, Viktor P.; Zatsikha, Yuriy V.; Rohde, Gregory T.; Nemykin, Victor N.; Kovtun, Yuriy P.; The Journal of organic chemistry 84 (2019) 2133–2147; doi:10.1021/acs.joc.8b03119

data_4033756
_publ_section_title
;
 Flexible BODIPY Platform That Offers an Unexpected Regioselective
 Heterocyclization Reaction toward Preparation of 2-Pyridone[ a]-Fused
 BODIPYs.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2133
_journal_page_last               2147
_journal_paper_doi               10.1021/acs.joc.8b03119
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C25 H31 B F2 N4 O3, C7 H8'
_chemical_formula_sum            'C32 H39 B F2 N4 O3'
_chemical_formula_weight         576.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.270(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1030(5)
_cell_length_b                   12.2789(3)
_cell_length_c                   16.4063(12)
_cell_measurement_reflns_used    8647
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      2.9
_cell_volume                     3029.7(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_av_unetI/netI     0.1659
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17365
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        58.936
_diffrn_reflns_theta_max         58.936
_diffrn_reflns_theta_min         2.938
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
FS_PROCESS, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         4307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.2199
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1350P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1392
_reflns_number_total             4307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03119_si_002.cif
_cod_data_source_block           08132016-1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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/c'
_cod_database_code               4033756
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              32106
_shelx_hkl_checksum              96357