Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C-H functionalization and their photophysical properties.
Shimada, Takahide; Mori, Shigeki; Ishida, Masatoshi; Furuta, Hiroyuki; Beilstein journal of organic chemistry 16 (2020) 587–595; doi:10.3762/bjoc.16.53

data_4038168
_publ_section_title
;
 Regioselectively \a- and \b-alkynylated BODIPY dyes via gold(I)-catalyzed
 direct C-H functionalization and their photophysical properties.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              587
_journal_page_last               595
_journal_paper_doi               10.3762/bjoc.16.53
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C40 H57 B F2 N2 Si2'
_chemical_formula_sum            'C40 H57 B F2 N2 Si2'
_chemical_formula_weight         670.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.750(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9534(4)
_cell_length_b                   8.04654(17)
_cell_length_c                   25.0121(5)
_cell_measurement_reflns_used    34722
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.18
_cell_measurement_theta_min      2.37
_cell_volume                     3931.69(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
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_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
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_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            64493
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.663
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_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
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_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         9499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0571
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_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+2.3671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7999
_reflns_number_total             9499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-53-S2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4038167--4038168.cif.'
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               4038168
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              87329
_shelx_hkl_checksum              5857