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_7133850
_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                 97.537(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.90570(10)
_cell_length_b                   15.6724(4)
_cell_length_c                   17.7952(5)
_cell_measurement_reflns_used    5344
_cell_measurement_temperature    93.00(10)
_cell_measurement_theta_max      76.0400
_cell_measurement_theta_min      3.7810
_cell_volume                     1632.83(7)
_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      93.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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     36.00 110.00   0.50    1.53    --  106.23 -77.00  30.00  148
  2  \w     46.00  71.00   0.50    1.53    --  106.23 -70.00  39.00   50
  3  \w     36.00  62.00   0.50    1.53    --  106.23-125.00   0.00   52
  4  \w     87.00 112.00   0.50    1.53    --  106.23-125.00   0.00   50
  5  \w     44.00  86.00   0.50    1.53    --  106.23-125.00  30.00   84
  6  \w    -15.00  58.00   0.50    0.36    --   45.96 -70.00  39.00  146
  7  \w     92.00 175.00   0.50    1.53    --  106.23  30.00-120.00  166
  8  \w     99.00 176.00   0.50    1.53    --  106.23  45.00  90.00  154
  9  \w    104.00 168.00   0.50    1.53    --  106.23  45.00 120.00  128
 10  \w     91.00 178.00   0.50    1.53    --  106.23  70.00 170.00  174
 11  \w     26.00 116.00   0.50    0.36    --   45.96  70.00 170.00  180
 12  \w    -18.00   8.00   0.50    0.36    --  -45.96  70.00 170.00   52
 13  \w    -80.00 -32.00   0.50    1.53    -- -104.50  70.00 170.00   96
 14  \w    -66.00 -34.00   0.50    1.53    -- -104.50  61.00 150.00   64
 15  \w    -20.00  26.00   0.50    0.36    --  -45.96  19.00 -30.00   92
 16  \w    -12.00  28.00   0.50    0.36    --  -45.96  19.00-180.00   80
 17  \w    -65.00 -32.00   0.50    1.53    -- -104.50  61.00-150.00   66
 18  \w    -65.00 -33.00   0.50    1.53    -- -104.50  61.00 -60.00   64
 19  \w    -66.00 -41.00   0.50    1.53    -- -104.50  61.00   0.00   50
 20  \w   -163.00-136.00   0.50    1.53    -- -104.50 -70.00  39.00   54
;
_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      0.0534026000
_diffrn_orient_matrix_UB_12      0.0200561000
_diffrn_orient_matrix_UB_13      -0.0806116000
_diffrn_orient_matrix_UB_21      -0.1529428000
_diffrn_orient_matrix_UB_22      -0.0748931000
_diffrn_orient_matrix_UB_23      -0.0314342000
_diffrn_orient_matrix_UB_31      -0.2071525000
_diffrn_orient_matrix_UB_32      0.0604520000
_diffrn_orient_matrix_UB_33      -0.0120586000
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9284
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         3.773
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.655
_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    1.522
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0208P)^2^+8.6349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2677
_reflns_number_total             2890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04416a2.cif
_cod_data_source_block           111-01-153_auto
_cod_depositor_comments
'Adding full bibliography for 7133850--7133853.cif.'
_cod_database_code               7133850
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNFBSCl
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.683
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00I(H00I),
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
;
_shelx_res_checksum              89399
_shelx_hkl_checksum              98690
_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 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.832