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_7133851
_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         'C21 H13 B F2 N2 S'
_chemical_formula_sum            'C21 H13 B F2 N2 S'
_chemical_formula_weight         374.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 111.763(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6699(2)
_cell_length_b                   10.8486(2)
_cell_length_c                   14.0687(3)
_cell_measurement_reflns_used    6124
_cell_measurement_temperature    92.99(10)
_cell_measurement_theta_max      73.6660
_cell_measurement_theta_min      4.2130
_cell_volume                     1654.18(6)
_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      92.99(10)
_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    -26.00  43.00   0.50    0.05    --   46.21 -55.00 -95.00  138
  2  \w     33.00  68.00   0.50    0.20    --  106.23 -55.00 -95.00   70
  3  \w     40.00  66.00   0.50    0.20    --  106.23 -61.00  30.00   52
  4  \w     33.00  61.00   0.50    0.20    --  106.23 -61.00  60.00   56
  5  \w     36.00  69.00   0.50    0.20    --  106.23 -61.00 150.00   66
  6  \w    109.00 178.00   0.50    0.20    --  106.23  45.00 150.00  138
  7  \w    148.00 178.00   0.50    0.20    --  106.23  55.00  47.00   60
  8  \w     36.00  79.00   0.50    0.20    --  106.23 -95.00   0.00   86
  9  \w     51.00 118.00   0.50    0.05    --   46.21  55.00  47.00  134
 10  \w    -14.00  27.00   0.50    0.05    --  -46.21  55.00  47.00   82
 11  \w    -21.00  29.00   0.50    0.05    --  -46.21  19.00  30.00  100
 12  \w    -21.00  28.00   0.50    0.05    --  -46.21  19.00-150.00   98
 13  \w    -96.00 -44.00   0.50    0.20    -- -104.50  77.00-120.00  104
 14  \w    -65.00 -39.00   0.50    0.20    -- -104.50  61.00-180.00   52
 15  \w    -64.00 -36.00   0.50    0.20    -- -104.50  61.00-150.00   56
 16  \w    -64.00 -39.00   0.50    0.20    -- -104.50  61.00 -90.00   50
 17  \w    -57.00 -31.00   0.50    0.20    -- -104.50  55.00  47.00   52
 18  \w    -60.00 -35.00   0.50    0.20    -- -104.50  61.00  90.00   50
 19  \w    -95.00 -43.00   0.50    0.20    -- -104.50 125.00  60.00  104
 20  \w   -174.00 -90.00   0.50    0.20    -- -104.50 -55.00 -95.00  168
 21  \w   -172.00-131.00   0.50    0.20    -- -104.50 -61.00   0.00   82
 22  \w   -174.00 -92.00   0.50    0.20    -- -104.50 -45.00 -30.00  164
 23  \w   -116.00 -91.00   0.50    0.20    -- -104.50 -61.00   0.00   50
 24  \w    -97.00 -65.00   0.50    0.05    --  -46.21 -55.00 -95.00   64
;
_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      0.1129086000
_diffrn_orient_matrix_UB_12      0.0861595000
_diffrn_orient_matrix_UB_13      0.0307760000
_diffrn_orient_matrix_UB_21      0.0353162000
_diffrn_orient_matrix_UB_22      -0.0384577000
_diffrn_orient_matrix_UB_23      0.1127015000
_diffrn_orient_matrix_UB_31      0.0787668000
_diffrn_orient_matrix_UB_32      -0.1060944000
_diffrn_orient_matrix_UB_33      -0.0159113000
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10472
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.054
_diffrn_reflns_theta_max         67.054
_diffrn_reflns_theta_min         4.225
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.853
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0473P)^2^+0.8089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2640
_reflns_number_total             2941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04416a2.cif
_cod_data_source_block           154annulation_auto
_cod_depositor_comments
'Adding full bibliography for 7133850--7133853.cif.'
_cod_database_code               7133851
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNBFS
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.741
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C6(H6), C18(H18), C25(H25), C19(H19), C4(H4), C5(H5), C21(H21),
 C24(H24), C22(H22), C12(H12), C10(H10), C23(H23)
;
_shelx_res_checksum              95681
_shelx_hkl_checksum              70414
_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.815