1,7-Dithienyl BODIPYs: Do Thienyls Outperform Phenyls?
Hotynchan, Andrii; Polishchuk, Vladyslav; Shishkina, Svitlana V.; Kulinich, Andrii Volodymyrovych; Kovtun, Yuriy P.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01656H

data_7160854
_publ_section_title
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 1,7-Dithienyl BODIPYs: Do Thienyls Outperform Phenyls?
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01656H
_journal_year                    2025
_chemical_formula_moiety         'C25 H23 B F2 N2 O4 S2'
_chemical_formula_sum            'C25 H23 B F2 N2 O4 S2'
_chemical_formula_weight         528.38
_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             2024-11-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-09-15 deposited with the CCDC.	2025-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.235(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.774(5)
_cell_length_b                   8.0609(19)
_cell_length_c                   30.271(7)
_cell_measurement_reflns_used    619
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.77
_cell_measurement_theta_min      2.86
_cell_volume                     4824(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.3640
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8498
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.030
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       plate
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         8498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.3027
_refine_ls_R_factor_gt           0.1162
_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^)+(0.0905P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3061
_reflns_number_total             8498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01656h2.cif
_cod_data_source_block           14
_cod_original_cell_volume        4824.1(19)
_cod_database_code               7160854
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.922(3)
 0.078(3)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C9A) = Uanis(C8A) = Uanis(C7A)
Uanis(C12A) = Uanis(C13A)
Uanis(B1A) = Uanis(N2A)
Uanis(B1B) = Uanis(N2B)
Uanis(C3A) = Uanis(C12A) = Uanis(C13A)
4.a Secondary CH2 refined with riding coordinates:
 C21A(H21A,H21B), C24A(H24A,H24B), C21B(H21C,H21D), C24B(H24C,H24D)
4.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C13A(H13A), C14A(H14A), C15A(H15A), C17A(H17A), C18A(H18A),
 C19A(H19A), C5B(H5B), C13B(H13B), C14B(H14B), C15B(H15B), C17B(H17B),
 C18B(H18B), C19B(H19B)
4.c Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C11A(H11A,H11B,H11C), C22A(H22A,H22B,H22C), C25A(H25A,
 H25B,H25C), C10B(H10D,H10E,H10F), C11B(H11D,H11E,H11F), C22B(H22D,H22E,H22F),
 C25B(H25D,H25E,H25F)
;
_shelx_res_checksum              9799
_olex2_submission_special_instructions 'No special instructions were received'