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_7133852
_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         'C23 H15 B F2 N2'
_chemical_formula_sum            'C23 H15 B F2 N2'
_chemical_formula_weight         368.18
_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             2024-07-10
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-19 deposited with the CCDC.	2024-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.915(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8694(2)
_cell_length_b                   16.1821(4)
_cell_length_c                   17.7533(4)
_cell_measurement_reflns_used    10464
_cell_measurement_temperature    93
_cell_measurement_theta_max      30.7510
_cell_measurement_theta_min      2.3110
_cell_volume                     1670.13(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 CCD
_diffrn_detector_type            'Rigaku Saturn-N'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.877
_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   -110.00  70.00   0.50   20.00    --  -20.00  45.00   0.00  360
  2  \w   -110.00  70.00   0.50   20.00    --  -20.00  45.00  90.00  360
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0326630000
_diffrn_orient_matrix_UB_12      -0.0140036000
_diffrn_orient_matrix_UB_13      0.0378041000
_diffrn_orient_matrix_UB_21      -0.0286561000
_diffrn_orient_matrix_UB_22      0.0391578000
_diffrn_orient_matrix_UB_23      0.0140003000
_diffrn_orient_matrix_UB_31      -0.1140361000
_diffrn_orient_matrix_UB_32      -0.0138360000
_diffrn_orient_matrix_UB_33      0.0013472000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15012
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.967
_diffrn_reflns_theta_min         2.316
_diffrn_source                   'rotating-anode X-ray tubee'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0449
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3949
_reflns_number_total             4657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04416a2.cif
_cod_data_source_block           111-01-060_autored
_cod_depositor_comments
'Adding full bibliography for 7133850--7133853.cif.'
_cod_database_code               7133852
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_shelx_res_checksum              59173
_shelx_hkl_checksum              17784
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.827