Replacing the BO in BODIPY: unlocking the path to SBDIPY and BIDIPY chromophores.
Korzun, André; Crespi, Stefano; Golz, Christopher; Bismuto, Alessandro; Chemical science 14 (2023) 6579–6584; doi:10.1039/d3sc01493b

data_1569330
_publ_section_title
;
 Replacing the BO in BODIPY: unlocking the path to SBDIPY and BIDIPY
 chromophores.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6579
_journal_page_last               6584
_journal_paper_doi               10.1039/d3sc01493b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C19 H19 Bi Cl2 N2'
_chemical_formula_sum            'C19 H19 Bi Cl2 N2'
_chemical_formula_weight         555.24
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-12
_audit_creation_method
;FinalCif V110 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.9835(6)
_cell_length_b                   22.9835(6)
_cell_length_c                   14.1686(4)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.456
_cell_measurement_theta_min      2.449
_cell_volume                     7484.4(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.14/2020-04-30'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            112176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.509
_diffrn_reflns_theta_min         2.448
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.711
_exptl_absorpt_correction_T_max  0.6495
_exptl_absorpt_correction_T_min  0.3150
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1279 before and 0.0477 after correction.
The Ratio of minimum to maximum transmission is 0.4850.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_description       block
_exptl_crystal_F_000             4224
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.056
_refine_diff_density_max         1.637
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         6239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0197P)^2^+21.7058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0438
_refine_ls_wR_factor_ref         0.0452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5682
_reflns_number_total             6239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01493b2.cif
_cod_data_source_block           mo_1768_cg_0m
_cod_original_cell_volume        7484.4(4)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               1569330
_shelx_shelxl_version_number     2018/3
_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), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.166
_shelx_estimated_absorpt_t_max   0.612
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              8824