Zig-zag-fused π-extended BODIPYs <i>via</i> gold-catalysed cycloisomerisation.
Ohashi, Fumika; Takano, Hideaki; Shinokubo, Hiroshi; Chemical communications (Cambridge, England) 60 (2024) 12892–12895; doi:10.1039/d4cc04416a

data_7133853
_publ_section_title
;
 Zig-zag-fused &#x3c0;-extended BODIPYs <i>via</i> gold-catalysed
 cycloisomerisation.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12892
_journal_page_last               12895
_journal_paper_doi               10.1039/d4cc04416a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C40 H24 B2 F4 N4'
_chemical_formula_sum            'C40 H24 B2 F4 N4'
_chemical_formula_weight         658.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-09
_audit_creation_method
;
Olex2 1.5-ac6-018
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_audit_update_record
;
2024-07-19 deposited with the CCDC.	2024-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                94.375(2)
_cell_angle_beta                 92.4060(10)
_cell_angle_gamma                112.285(2)
_cell_formula_units_Z            4
_cell_length_a                   11.2443(2)
_cell_length_b                   12.5476(3)
_cell_length_c                   23.0507(4)
_cell_measurement_reflns_used    16101
_cell_measurement_temperature    93.01(13)
_cell_measurement_theta_max      74.8180
_cell_measurement_theta_min      3.8290
_cell_volume                     2991.65(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.113a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.113a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.113a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      93.01(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -74.00   9.00   0.50    0.33    --  -45.96  89.00-110.00  166
  2  \w    -24.00  71.00   0.50    0.33    --   45.96 -89.00 133.00  190
  3  \w   -141.00 -79.00   0.50    1.31    -- -104.50 -89.00 133.00  124
  4  \w    -91.00 -38.00   0.50    1.31    -- -104.50  89.00-110.00  106
  5  \w     65.00 104.00   0.50    1.31    --  106.23 -89.00 133.00   78
  6  \w     87.00 169.00   0.50    1.31    --  106.23  89.00-110.00  164
  7  \w    -37.00  28.00   0.50    0.33    --  -45.96  38.00-180.00  130
  8  \w    -37.00  16.00   0.50    0.33    --  -45.96  38.00  60.00  106
  9  \w    -10.00  23.00   0.50    0.33    --  -45.96  19.00  60.00   66
 10  \w    -52.00 -14.00   0.50    0.33    --  -45.96 125.00 -30.00   76
 11  \w    -21.00  29.00   0.50    0.33    --  -45.96  19.00 150.00  100
 12  \w    -21.00   4.00   0.50    0.33    --  -45.96  19.00 -30.00   50
 13  \w    -21.00  48.00   0.50    0.33    --   45.96 -38.00-180.00  138
 14  \w   -129.00-103.00   0.50    1.31    -- -104.50 150.00  92.46   52
 15  \w   -123.00 -97.00   0.50    1.31    -- -104.50 142.00 -60.05   52
 16  \w   -146.00 -90.00   0.50    1.31    -- -104.50 -61.00  90.00  112
 17  \w    -83.00 -57.00   0.50    1.31    -- -104.50 150.00  92.46   52
 18  \w   -153.00-128.00   0.50    1.31    -- -104.50 -45.00 -90.00   50
 19  \w   -109.00 -35.00   0.50    1.31    -- -104.50 125.00-120.00  148
 20  \w    -74.00 -31.00   0.50    1.31    -- -104.50 142.00 -60.05   86
 21  \w    -65.00 -31.00   0.50    1.31    -- -104.50  61.00-120.00   68
 22  \w   -123.00 -88.00   0.50    1.31    -- -104.50 -61.00-180.00   70
 23  \w   -138.00 -87.00   0.50    1.31    -- -104.50 -15.00-150.00  102
 24  \w   -173.00-128.00   0.50    1.31    -- -104.50 -61.00-180.00   90
 25  \w    -62.00 -34.00   0.50    1.31    -- -104.50  61.00  60.00   56
 26  \w    -99.00 -57.00   0.50    1.31    -- -104.50  77.00   0.00   84
 27  \w    -66.00 -32.00   0.50    1.31    -- -104.50  61.00  30.00   68
 28  \w     33.00 105.00   0.50    1.31    --  106.23 -95.00   0.00  144
 29  \w     38.00  99.00   0.50    1.31    --  106.23-125.00-180.00  122
 30  \w     40.00  97.00   0.50    1.31    --  106.23 -95.00  60.00  114
 31  \w     37.00 112.00   0.50    1.31    --  106.23-125.00   0.00  150
 32  \w     75.00 102.00   0.50    1.31    --  106.23 -95.00  90.00   54
 33  \w     47.00 106.00   0.50    1.31    --  106.23-100.00-128.43  118
 34  \w     89.00 164.00   0.50    1.31    --  106.23  61.00 -60.00  150
 35  \w     47.00  73.00   0.50    1.31    --  106.23-125.00 120.00   52
 36  \w     41.00  66.00   0.50    1.31    --  106.23 -61.00 -90.00   50
 37  \w     91.00 176.00   0.50    1.31    --  106.23  61.00-180.00  170
 38  \w     87.00 112.00   0.50    1.31    --  106.23-125.00 -90.00   50
 39  \w     37.00  64.00   0.50    1.31    --  106.23-125.00 -90.00   54
 40  \w     87.00 112.00   0.50    1.31    --  106.23-125.00 120.00   50
 41  \w     87.00 178.00   0.50    1.31    --  106.23  77.00 150.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024849000
_diffrn_orient_matrix_UB_12      0.0630737000
_diffrn_orient_matrix_UB_13      0.0596774000
_diffrn_orient_matrix_UB_21      -0.1222959000
_diffrn_orient_matrix_UB_22      -0.1027182000
_diffrn_orient_matrix_UB_23      0.0121254000
_diffrn_orient_matrix_UB_31      0.0842115000
_diffrn_orient_matrix_UB_32      -0.0570394000
_diffrn_orient_matrix_UB_33      0.0284805000
_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  0.0388
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35319
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.826
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.113a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         10630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0733P)^2^+3.6976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1666
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9332
_reflns_number_total             10630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04416a2.cif
_cod_data_source_block           188_auto
_cod_depositor_comments
'Adding full bibliography for 7133850--7133853.cif.'
_cod_original_cell_volume        2991.64(11)
_cod_database_code               7133853
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNBFCl
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.829
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00P(H00P), C00V(H00V), C00W(H00W), C00X(H00X), C011(H011), C012(H012),
 C015(H015), C019(H019), C01A(H01A), C01C(H01C), C01G(H01G), C01H(H01H),
 C01J(H01J), C01L(H01L), C01N(H01N), C01P(H01P), C01R(H01R), C01S(H01S),
 C01U(H01U), C01W(H01W), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020),
 C021(H021), C022(H022), C023(H023), C024(H024), C025(H025), C026(H026),
 C027(H027), C028(H028), C029(H029), C02A(H02A), C02B(H02B), C02C(H02C),
 C02D(H02D), C02E(H02E), C02F(H02F), C02G(H02G), C02H(H02H), C02I(H02I),
 C02J(H02J), C02K(H02K), C02L(H02L), C02M(H02M), C02N(H02N), C02O(H02O)
;
_shelx_res_checksum              64670
_shelx_hkl_checksum              41233
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.737