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_1569326
_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         'C17 H23 Bi Cl2 N2 O'
_chemical_formula_sum            'C17 H23 Bi Cl2 N2 O'
_chemical_formula_weight         551.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-22
_audit_creation_method
;FinalCif V108 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                 95.441(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7403(9)
_cell_length_b                   9.2435(6)
_cell_length_c                   22.984(3)
_cell_measurement_reflns_used    1040
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      22.87
_cell_measurement_theta_min      2.34
_cell_volume                     1848.5(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2021.4-0'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Ag'
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            46052
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.757
_diffrn_reflns_theta_min         2.341
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.832
_exptl_absorpt_correction_T_max  0.7694
_exptl_absorpt_correction_T_min  0.4930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.6408.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.034
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         6909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0086P)^2^+2.1124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0324
_refine_ls_wR_factor_ref         0.0348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6071
_reflns_number_total             6909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01493b2.cif
_cod_data_source_block           mo_1749_cg_0m
_cod_depositor_comments
;

2025-07-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H46 Bi2 Cl4 N4 O2'
_cod_original_formula_weight         1102.51
_cod_original_formula_moiety         'C34 H46 Bi2 Cl4 N4 O2'
_cod_original_formula_units_Z            2
_cod_database_code               1569326
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.309
_shelx_estimated_absorpt_t_max   0.731
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              51237