Fluorinated and methylated <i>ortho</i>-benzodipyrrole-based acceptors suppressing charge recombination and minimizing energy loss in organic photovoltaics.
Wang, Yan-Bo; Tsai, Chia-Lin; Xue, Yung-Jing; Jiang, Bing-Huang; Lu, Han-Cheng; Hong, Jun-Cheng; Huang, Yu-Chi; Huang, Kuo-Hsiu; Chien, Su-Ying; Chen, Chih-Ping; Cheng, Yen-Ju; Chemical science 16 (2025) 3259–3274; doi:10.1039/d4sc07146h

data_1573622
_publ_section_title
;
 Fluorinated and methylated <i>ortho</i>-benzodipyrrole-based acceptors
 suppressing charge recombination and minimizing energy loss in organic
 photovoltaics.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              3259
_journal_page_last               3274
_journal_paper_doi               10.1039/d4sc07146h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C98 H118 F6 N6 O2 S4'
_chemical_formula_weight         1654.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-10-17 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.2920(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.2111(8)
_cell_length_b                   22.7564(8)
_cell_length_c                   33.5239(11)
_cell_measurement_reflns_used    13848
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.52
_cell_measurement_theta_min      2.20
_cell_volume                     18261.3(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            48466
_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         25.249
_diffrn_reflns_theta_min         1.901
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       needle
_exptl_crystal_F_000             7056
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.227
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1043
_refine_ls_number_reflns         16533
_refine_ls_number_restraints     828
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.3081
_refine_ls_R_factor_gt           0.1997
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1899P)^2^+130.4250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4729
_refine_ls_wR_factor_ref         0.5593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6091
_reflns_number_total             16533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07146h2.cif
_cod_data_source_block           ic22087_sq
_cod_depositor_comments
'Adding full bibliography for 1573622--1573623.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1573622
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              33226
_shelx_hkl_checksum              68542
_shelx_fab_checksum              51141