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_7132336
_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         'C20 H15 B F2 N2'
_chemical_formula_sum            'C20 H15 B F2 N2'
_chemical_formula_weight         332.15
_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             2022-05-02
_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                 106.696(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2668(3)
_cell_length_b                   15.3965(4)
_cell_length_c                   9.5029(3)
_cell_measurement_reflns_used    29179
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.2070
_cell_measurement_theta_min      4.0720
_cell_volume                     1578.97(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -64.00  23.00   0.50    1.50    --  -48.54  64.00 118.00  174
  2  \w   -120.00 -33.00   0.50    1.50    --  -48.54 -64.00 -18.00  174
  3  \w    -22.00  64.00   0.50    1.50    --   48.54 -64.00 -18.00  172
  4  \w   -177.00 -90.00   0.50    6.00    -- -105.75 -64.00 -18.00  174
  5  \w    -78.00 -34.00   0.50    6.00    -- -105.75  64.00 118.00   88
  6  \w     90.00 178.00   0.50    6.00    --  105.75  64.00 118.00  176
  7  \w     34.00  74.00   0.50    6.00    --  105.75 -64.00 -18.00   80
  8  \w    -28.00  25.00   0.50    1.50    --  -48.54  19.00 -60.00  106
  9  \w   -120.00 -73.00   0.50    1.50    --  -48.54-125.00-120.00   94
 10  \w     74.00 121.00   0.50    1.50    --   48.54 125.00 -30.00   94
 11  \w     41.00 122.00   0.50    1.50    --   48.54  19.00 -90.00  162
 12  \w     74.00 121.00   0.50    1.50    --   48.54 125.00-150.00   94
 13  \w     33.00 121.00   0.50    1.50    --   48.54  64.00 118.00  176
 14  \w   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 -90.00  184
 15  \w   -177.00 -91.00   0.50    6.00    -- -105.75 -61.00-120.00  172
 16  \w     34.00 105.50   0.50    6.00    --  105.75-125.00 -90.00  143
 17  \w     34.00  69.00   0.50    6.00    --  105.75 -61.00  60.00   70
 18  \w     34.00 103.00   0.50    6.00    --  105.75 -77.00 -90.00  138
 19  \w     85.00 178.00   0.50    6.00    --  105.75  77.00  60.00  186
 20  \w     92.00 178.00   0.50    6.00    --  105.75  61.00-180.00  172
 21  \w     34.00 106.00   0.50    6.00    --  105.75 -94.00 -30.00  144
 22  \w     34.00  69.00   0.50    6.00    --  105.75 -61.00 120.00   70
 23  \w     92.00 178.00   0.50    6.00    --  105.75  61.00  90.00  172
 24  \w     74.00 178.00   0.50    6.00    --  105.75 125.00  90.00  208
 25  \w     98.00 178.00   0.50    6.00    --  105.75  30.00  60.00  160
 26  \w     34.00 103.00   0.50    6.00    --  105.75 -77.00  30.00  138
 27  \w     98.00 178.00   0.50    6.00    --  105.75  30.00  30.00  160
 28  \w     92.00 178.00   0.50    6.00    --  105.75  61.00 150.00  172
 29  \w     92.00 178.00   0.50    6.00    --  105.75  61.00 -90.00  172
 30  \w     85.00 178.00   0.50    6.00    --  105.75  77.00-120.00  186
 31  \w     98.00 178.00   0.50    6.00    --  105.75  30.00-180.00  160
 32  \w     34.00  69.00   0.50    6.00    --  105.75 -61.00-120.00   70
 33  \w     92.00 178.00   0.50    6.00    --  105.75  61.00-150.00  172
 34  \w     92.00 178.00   0.50    6.00    --  105.75  61.00-120.00  172
 35  \w     34.00 103.00   0.50    6.00    --  105.75 -77.00   0.00  138
 36  \w     34.00  69.00   0.50    6.00    --  105.75 -61.00-150.00   70
 37  \w     34.00  69.00   0.50    6.00    --  105.75 -61.00 150.00   70
 38  \w   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00  60.00  184
 39  \w   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00 -90.00  184
 40  \w   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00 120.00  184
 41  \w   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00-150.00  184
 42  \w   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00 -30.00  184
 43  \w   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00-180.00  184
 44  \w     36.00 121.00   0.50    1.50    --   48.54  57.00  30.00  170
 45  \w     41.00 121.00   0.50    1.50    --   48.54  37.00 -60.00  160
 46  \w     41.00 121.00   0.50    1.50    --   48.54  37.00   0.00  160
 47  \w    -23.00  40.00   0.50    1.50    --   48.54 -37.00-180.00  126
 48  \w   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 120.00  184
 49  \w   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 -30.00  184
 50  \w   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00-150.00  184
 51  \w   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 150.00  184
 52  \w     85.00 178.00   0.50    6.00    --  105.75  77.00  30.00  186
 53  \w     92.00 178.00   0.50    6.00    --  105.75  61.00  60.00  172
 54  \w     34.00 111.00   0.50    6.00    --  105.75-125.00-180.00  154
 55  \w     92.00 178.00   0.50    6.00    --  105.75  61.00 -60.00  172
 56  \w     34.00 106.00   0.50    6.00    --  105.75 -94.00 -60.00  144
 57  \w     85.00 178.00   0.50    6.00    --  105.75  77.00 -60.00  186
 58  \w     34.00 111.00   0.50    6.00    --  105.75-125.00-150.00  154
 59  \w     85.00 178.00   0.50    6.00    --  105.75  77.00-180.00  186
 60  \w     85.00 178.00   0.50    6.00    --  105.75  77.00 120.00  186
 61  \w     85.00 178.00   0.50    6.00    --  105.75  77.00 -30.00  186
 62  \w     34.00  69.00   0.50    6.00    --  105.75 -61.00-180.00   70
 63  \w     34.00 103.00   0.50    6.00    --  105.75 -77.00  60.00  138
 64  \w     85.00 178.00   0.50    6.00    --  105.75  77.00  90.00  186
 65  \w     34.00 106.00   0.50    6.00    --  105.75 -94.00  30.00  144
 66  \w     92.00 178.00   0.50    6.00    --  105.75  61.00  30.00  172
 67  \w     34.00 100.00   0.50    6.00    --  105.75 -94.00-180.00  132
 68  \w     85.00 178.00   0.50    6.00    --  105.75  77.00   0.00  186
 69  \w     92.00 178.00   0.50    6.00    --  105.75  61.00 -30.00  172
 70  \w     85.00 178.00   0.50    6.00    --  105.75  77.00 -90.00  186
 71  \w     85.00 178.00   0.50    6.00    --  105.75  77.00 150.00  186
 72  \w     92.00 178.00   0.50    6.00    --  105.75  61.00   0.00  172
 73  \w     85.00 178.00   0.50    6.00    --  105.75  77.00-150.00  186
 74  \w     34.00  69.00   0.50    6.00    --  105.75 -61.00  90.00   70
 75  \w     34.00  99.00   0.50    6.00    --  105.75 -94.00-120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0589644000
_diffrn_orient_matrix_UB_12      -0.0478421000
_diffrn_orient_matrix_UB_13      -0.1055624000
_diffrn_orient_matrix_UB_21      -0.1173407000
_diffrn_orient_matrix_UB_22      -0.0562502000
_diffrn_orient_matrix_UB_23      -0.0546673000
_diffrn_orient_matrix_UB_31      -0.0559753000
_diffrn_orient_matrix_UB_32      0.0675129000
_diffrn_orient_matrix_UB_33      -0.1204550000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            64031
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        77.000
_diffrn_reflns_theta_max         77.738
_diffrn_reflns_theta_min         4.096
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00086(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0331P)^2^+0.8828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3266
_reflns_number_total             3337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04913b2.cif
_cod_data_source_block           gefhalf
_cod_database_code               7132336
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H15 B F2 N2'
_chemical_oxdiff_usercomment     'Geffers/Werz FG6-568'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.931
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              88306
_shelx_hkl_checksum              73672
_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 1.269
_oxdiff_exptl_absorpt_empirical_full_min 0.836