Access to isoindole-derived BODIPYs by an aminopalladation cascade
von Köller, Heinrich; Geffers, Finn; Kalvani, Pedram; Foraita, Adrian; Loß, Patrick-Eric; Butschke, Burkhard; Jones, P. G.; Werz, Daniel B.; Chemical Communications  (2023) –; doi:10.1039/D3CC04913B

data_7132337
_publ_section_title
;
 Access to isoindole-derived BODIPYs by an aminopalladation cascade
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04913B
_journal_year                    2023
_chemical_formula_moiety         'C19 H14 B F2 N3'
_chemical_formula_sum            'C19 H14 B F2 N3'
_chemical_formula_weight         333.14
_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
_atom_sites_solution_primary     intrinsic
_audit_creation_date             2022-04-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-10-02 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.535(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2238(3)
_cell_length_b                   15.6385(4)
_cell_length_c                   9.2476(3)
_cell_measurement_reflns_used    62015
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      38.2570
_cell_measurement_theta_min      2.2860
_cell_volume                     1556.05(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    SHELXT
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     16.00  96.00   0.50   20.00    --   22.89  19.00 -71.00  160
  2  \w    -49.00   5.00   0.50   20.00    --   22.89 -19.00 120.00  108
  3  \w    -31.00  50.00   0.50   20.00    --  -23.67  19.00 -71.00  162
  4  \w    -97.00 -16.00   0.50   20.00    --  -23.67 -19.00 120.00  162
  5  \w      2.00  95.00   0.50   20.00    --   22.89  77.00 -90.00  186
  6  \w      2.00  95.00   0.50   20.00    --   22.89  77.00  30.00  186
  7  \w      2.00  95.00   0.50   20.00    --   22.89  77.00-150.00  186
  8  \w    -49.00   5.00   0.50   20.00    --   22.89 -19.00  90.00  108
  9  \w     15.00  95.00   0.50   20.00    --   22.89  37.00  60.00  160
 10  \w    -59.00   2.00   0.50   20.00    --  -23.67 106.00 -53.95  122
 11  \w    -61.00  -1.00   0.50   20.00    --  -23.67 110.00-130.67  120
 12  \w    -66.00  -9.00   0.50   20.00    --  -23.67 119.00 110.02  114
 13  \w    -61.00  -1.00   0.50   20.00    --  -23.67 110.00 145.74  120
 14  \w    -59.00   2.00   0.50   20.00    --  -23.67 106.00 101.52  122
 15  \w    -64.00  -6.00   0.50   20.00    --  -23.67 115.00 -16.16  116
 16  \w    -62.00  -2.00   0.50   20.00    --  -23.67 111.00  22.41  120
 17  \w    -95.00  -3.00   0.50   20.00    --  -23.67 -77.00  90.00  184
 18  \w    -56.00  18.00   0.50   20.00    --  -23.67 101.00-150.21  148
 19  \w    -64.00  -6.00   0.50   20.00    --  -23.67 115.00-100.92  116
 20  \w    -95.00 -11.00   0.50   20.00    --  -23.67 -57.00  90.00  168
 21  \w    -49.00   5.00   0.50   20.00    --   22.89 -19.00   0.00  108
 22  \w     15.00  95.00   0.50   20.00    --   22.89  37.00-150.00  160
 23  \w     15.00  95.00   0.50   20.00    --   22.89  37.00   0.00  160
 24  \w    -64.00  -6.00   0.50   20.00    --  -23.67 116.00  53.90  116
 25  \w    -71.00 -15.00   0.50   20.00    --  -23.67 129.00 173.78  112
 26  \w    -63.00  -5.00   0.50   20.00    --  -23.67 114.00  45.23  116
 27  \w    -67.00 -10.00   0.50   20.00    --  -23.67 121.00 149.30  114
 28  \w    -65.00  -7.00   0.50   20.00    --  -23.67 117.00-122.05  116
 29  \w    -64.00  -6.00   0.50   20.00    --  -23.67 116.00 -76.30  116
 30  \w    -64.00  -6.00   0.50   20.00    --  -23.67 115.00  93.93  116
 31  \w    -72.00 -16.00   0.50   20.00    --  -23.67 130.00 -18.35  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0560615000
_diffrn_orient_matrix_UB_12      -0.0101872000
_diffrn_orient_matrix_UB_13      -0.0558546000
_diffrn_orient_matrix_UB_21      0.0333680000
_diffrn_orient_matrix_UB_22      -0.0046977000
_diffrn_orient_matrix_UB_23      -0.0541439000
_diffrn_orient_matrix_UB_31      0.0094479000
_diffrn_orient_matrix_UB_32      -0.0439428000
_diffrn_orient_matrix_UB_33      0.0187639000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            142487
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        36.000
_diffrn_reflns_theta_max         36.316
_diffrn_reflns_theta_min         2.298
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         7548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0811P)^2^+0.1936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6027
_reflns_number_total             7548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04913b2.cif
_cod_data_source_block           gefbrau
_cod_original_cell_volume        1556.04(8)
_cod_database_code               7132337
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H14 B F2 N3'
_chemical_oxdiff_usercomment     'Geffers/Werz FG7-646'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H1D(0.5) H1E(0.5) H1F(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18)
3.b Disordered Me refined as rotating group:
 C1(H1A,H1B,H1C,H1D,H1E,H1F)
;
_shelx_res_checksum              69578
_shelx_hkl_checksum              60744
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.858