BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies.
Zaitsev, Andrei V.; Kiselev, Sergey S.; Smol'yakov, Alexander F.; Fedorov, Yury V.; Kononova, Elena G.; Borisov, Yurii A.; Ol'shevskaya, Valentina A.; Organic & biomolecular chemistry 21 (2023) 4084–4094; doi:10.1039/d3ob00255a

data_7159331
_publ_section_title
;
 BODIPY derivatives modified with carborane clusters: synthesis,
 characterization and DFT studies.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4084
_journal_page_last               4094
_journal_paper_doi               10.1039/d3ob00255a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H37 B31 F6 N2 S3'
_chemical_formula_sum            'C21 H37 B31 F6 N2 S3'
_chemical_formula_weight         862.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-17 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                89.765(2)
_cell_angle_beta                 78.137(2)
_cell_angle_gamma                89.937(2)
_cell_formula_units_Z            4
_cell_length_a                   12.4978(4)
_cell_length_b                   12.7398(4)
_cell_length_c                   26.8939(8)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.595
_cell_measurement_theta_min      2.31
_cell_volume                     4190.5(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41486
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.686
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.6475
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1071 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.8201.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       plate
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1163
_refine_ls_number_reflns         16401
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.1220
_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^)+55.6044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2832
_refine_ls_wR_factor_ref         0.2870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14508
_reflns_number_total             16401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00255a2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7159331--7159332.cif.'
_cod_database_code               7159331
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.922
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(S2A) \\sim Ueq, Uanis(S1B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(S1A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Others
 Sof(S1A)=Sof(S2A)=Sof(S1B)=1-FVAR(1)
 Sof(S1AR)=Sof(S2AR)=Sof(S1BR)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C7A(H7A), C8A(H8A), C2B(H2B), C3B(H3B), C7B(H7B), C8B(H8B)
4.b Boron cage BH refined with riding coordinates:
 C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A),
 B2A(H2AA), B3A(H3AA), B4A(H4A), B5A(H5A), B6A(H6A), B7A(H7AA), B8A(H8AA),
 B9A(H9A), B10A(H10A), B12A(H12A), B13A(H13A), B14A(H14A), B15A(H15A),
 B16A(H16B), B17A(H17B), B18A(H18B), B19A(H19B), B20A(H20B), B22A(H22A),
 B23A(H23A), B24A(H24A), B25A(H25A), B26A(H26A), B27A(H27A), B28A(H28A),
 B29A(H29A), B30A(H30A), C16B(H16C), C17B(H17C), C18B(H18C), C19B(H19C),
 C20B(H20C), C21B(H21B), B2B(H2BA), B02Y(H02Y), B3B(H3BA), B4B(H4B), B5B(H5B),
 B6B(H6B), B7B(H7BA), B8B(H8BA), B9B(H9B), B10B(H10B), B12B(H12B), B13B(H13B),
 B14B(H14B), B15B(H15B), B16B(H16D), B17B(H17D), B18B(H18D), B19B(H19D),
 B20B(H20D), B22B(H22B), B23B(H23B), B24B(H24B), B25B(H25B), B26B(H26B),
 B27B(H27B), B28B(H28B), B29B(H29B)
;
_shelx_res_checksum              29885
_olex2_submission_special_instructions 'No special instructions were received'