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_4038167
_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         'C44 H65 B F2 N2 Si2'
_chemical_formula_sum            'C44 H65 B F2 N2 Si2'
_chemical_formula_weight         726.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 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                 100.114(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.9498(8)
_cell_length_b                   21.4322(5)
_cell_length_c                   12.1761(3)
_cell_measurement_reflns_used    28428
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.23
_cell_measurement_theta_min      1.90
_cell_volume                     8721.9(4)
_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)'
_computing_molecular_graphics    'CrystalStructure 4.3.2 (Rigaku, 2019)'
_computing_publication_material  'CrystalStructure 4.3.2 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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 0.999
_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  0.0836
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            74283
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.699
_diffrn_source                   'rotating anode X-ray generator'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.751
_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            red
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3152
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 5331 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     958
_refine_ls_number_reflns         21044
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0640
_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^)+(0.0872P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                15105
_reflns_number_total             21044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-53-S3.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4038167--4038168.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4038167
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              91349
_shelx_hkl_checksum              93587