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_1569332
_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         'C13 H15 Cl N2 Sb, C32 H12 B F24, 1.5(C6 H6)'
_chemical_formula_sum            'C54 H36 B Cl F24 N2 Sb'
_chemical_formula_weight         1336.86
_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             2022-06-29
_audit_creation_method
;
FinalCif V106 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                79.607(7)
_cell_angle_beta                 75.288(7)
_cell_angle_gamma                80.032(7)
_cell_formula_units_Z            2
_cell_length_a                   12.379(4)
_cell_length_b                   12.587(4)
_cell_length_c                   18.983(6)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.773
_cell_measurement_theta_min      2.224
_cell_volume                     2788.6(15)
_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 0.994
_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  0.0577
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            84600
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.959
_diffrn_reflns_theta_min         2.132
_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    0.661
_exptl_absorpt_correction_T_max  0.3985
_exptl_absorpt_correction_T_min  0.3489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.8755.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       plate
_exptl_crystal_F_000             1326
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     947
_refine_ls_number_reflns         13335
_refine_ls_number_restraints     161
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+2.6364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10899
_reflns_number_total             13335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01493b2.cif
_cod_data_source_block           mo_1708_cg_0m
_cod_original_cell_volume        2788.7(14)
_cod_database_code               1569332
_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. Restrained distances
 C24-C23 = C21-C20 = C20-C25
 1.37 with sigma of 0.02
 C24-C25
 1.38 with sigma of 0.02
 C23-C22 = C22-C21
 1.36 with sigma of 0.02
 C24-C20
 2.38 with sigma of 0.04
 C24-C22 = C22-C20 = C21-C25
 2.37 with sigma of 0.04
 C23-C21
 2.36 with sigma of 0.04
 F22A-C57 \\sim F22B-C57
 with sigma of 0.02
 F18A-C41 \\sim F18B-C41
 with sigma of 0.02
 F23A-C57 \\sim F23B-C57
 with sigma of 0.02
 F24A-C57 \\sim F24B-C57
 with sigma of 0.02
 F21A-C56 \\sim F21B-C56
 with sigma of 0.02
 F19A-C56 \\sim F19B-C56
 with sigma of 0.02
 F20A-C56 \\sim F20B-C56
 with sigma of 0.02
 F16A-C41 \\sim F16B-C41
 with sigma of 0.02
 F17A-C41 \\sim F17B-C41
 with sigma of 0.02
 F2A-C32 \\sim F3B-C32
 with sigma of 0.02
 F3A-C32 \\sim F1B-C32
 with sigma of 0.02
 F1A-C32 \\sim F2B-C32
 with sigma of 0.02
 C33-F5A \\sim C33-F5B
 with sigma of 0.02
 C33-F6A \\sim C33-F6B
 with sigma of 0.02
 F7A-C48 \\sim F7B-C48
 with sigma of 0.02
 C33-F4A \\sim C33-F4B
 with sigma of 0.02
 F8A-C48 \\sim F8B-C48
 with sigma of 0.02
 F9A-C48 \\sim F9B-C48
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F21B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 F17B, F16B, F18B, C41
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F23B, C57, F24B, F22B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
 C56, F19B, F21B, F20B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F16A, F17A, F18A, C41
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3B, F2B, C32, F1B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 F6B, C33, F5B, F4B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F7B, C48, F8B, F9B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(F6B)=Sof(F5B)=Sof(F4B)=1-FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(1)
 Sof(F3B)=Sof(F2B)=Sof(F1B)=1-FVAR(2)
 Sof(F2A)=Sof(F1A)=Sof(F3A)=FVAR(2)
 Sof(F19B)=Sof(F20B)=Sof(F21B)=1-FVAR(3)
 Sof(F19A)=Sof(F20A)=Sof(F21A)=FVAR(3)
 Sof(F24B)=Sof(F23B)=Sof(F22B)=1-FVAR(4)
 Sof(F22A)=Sof(F23A)=Sof(F24A)=FVAR(4)
 Sof(F8B)=Sof(F7B)=Sof(F9B)=1-FVAR(5)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(5)
 Sof(F17B)=Sof(F16B)=Sof(F18B)=1-FVAR(6)
 Sof(F16A)=Sof(F17A)=Sof(F18A)=FVAR(6)
 Fixed Sof: C20(0.5) H20(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5) C23(0.5)
 H23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C27(H27), C29(H29), C31(H31), C35(H35), C37(H37),
 C39(H39), C43(H43), C45(H45), C47(H47), C51(H51), C53(H53), C55(H55), C14(H14),
  C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25)
6.b 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   0.916
_shelx_estimated_absorpt_t_max   0.972
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              65402