C-shaped ortho-benzodipyrrole-based acceptors with different electronic effects of top substituents for as-cast green-solvent processed high-performance organic solar cells
Gong, Yufei; Zou, Tianwei; Li, Xiaojun; Qin, Shucheng; Sun, Guangpei; Liang, TongLing; Zhou, Ruimin; Zhang, Jianqi; Zhang, Jinyuan; Meng, Lei; Wei, Zhixiang; Li, Yongfang; Energy & Environmental Science 17 (2024) 6844–6855; doi:10.1039/D4EE02467B

data_1572792
_publ_section_title
;
 C-shaped ortho-benzodipyrrole-based acceptors with different electronic
 effects of top substituents for as-cast green-solvent processed
 high-performance organic solar cells
;
_journal_issue                   18
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              6844
_journal_page_last               6855
_journal_paper_doi               10.1039/D4EE02467B
_journal_volume                  17
_journal_year                    2024
_chemical_formula_moiety         'C81 H72 Cl4 F2 N6 O2 S4, 0.125[]'
_chemical_formula_sum            'C81 H78 Cl4 F2 N6 O2 S4'
_chemical_formula_weight         1475.53
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jbct2
_audit_creation_date             2024-07-10
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-10 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.264(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2910(9)
_cell_length_b                   23.969(2)
_cell_length_c                   33.8600(12)
_cell_measurement_reflns_used    8731
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      70.6690
_cell_measurement_theta_min      2.6750
_cell_volume                     18826.2(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -58.00 -32.00   0.50    5.00    --  -46.42  96.00-124.00   52
  2  \w    -28.00  25.00   0.50    5.00    --  -46.42  96.00-124.00  106
  3  \w     14.00  58.00   0.50    5.00    --   46.42 -96.00 127.00   88
  4  \w    -21.00   7.00   0.50    5.00    --   46.42 -96.00 127.00   56
  5  \w   -104.00 -58.00   0.50   20.00    -- -104.50  96.00-124.00   92
  6  \w    108.00 178.00   0.50   20.00    --  108.85  96.00-124.00  140
  7  \w    -23.00   2.00   0.50    5.00    --  -46.42  19.00  60.00   50
  8  \w    -23.00  29.00   0.50    5.00    --  -46.42  19.00-150.00  104
  9  \w    -18.00   9.00   0.50    5.00    --  -46.42  19.00 150.00   54
 10  \w    -17.00  12.00   0.50    5.00    --  -46.42  19.00 -30.00   58
 11  \w    -27.00  46.00   0.50    5.00    --   46.42 -38.00 -90.00  146
 12  \w    -67.00 -42.00   0.50   20.00    -- -104.50  61.00 -30.00   50
 13  \w    -67.00 -32.00   0.50   20.00    -- -104.50  61.00-150.00   70
 14  \w    -59.00 -32.00   0.50   20.00    -- -104.50  61.00  60.00   54
 15  \w    -85.00 -38.00   0.50   20.00    -- -104.50  77.00  30.00   94
 16  \w    -67.00 -39.00   0.50   20.00    -- -104.50  61.00 -90.00   56
 17  \w   -171.00 -95.00   0.50   20.00    -- -104.50 -30.00 150.00  152
 18  \w    -67.00 -31.00   0.50   20.00    -- -104.50  61.00  90.00   72
 19  \w   -157.00-108.00   0.50   20.00    -- -104.50 -96.00 127.00   98
 20  \w    -68.00 -43.00   0.50   20.00    -- -104.50  61.00 120.00   50
 21  \w     38.00  66.00   0.50   20.00    --  108.85 -61.00 120.00   56
 22  \w     52.00  78.00   0.50   20.00    --  108.85-125.00  60.00   52
 23  \w     42.00  72.00   0.50   20.00    --  108.85 -61.00 -60.00   60
 24  \w    144.00 177.00   0.50   20.00    --  108.85  45.00-150.00   66
 25  \w     38.00  73.00   0.50   20.00    --  108.85 -61.00 -30.00   70
 26  \w     36.00  75.00   0.50   20.00    --  108.85 -61.00 -90.00   78
 27  \w     97.00 135.00   0.50   20.00    --  108.85  45.00-150.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0224632000
_diffrn_orient_matrix_UB_12      0.0600863000
_diffrn_orient_matrix_UB_13      -0.0096616000
_diffrn_orient_matrix_UB_21      -0.0173896000
_diffrn_orient_matrix_UB_22      0.0011835000
_diffrn_orient_matrix_UB_23      0.0402227000
_diffrn_orient_matrix_UB_31      0.0600234000
_diffrn_orient_matrix_UB_32      0.0227596000
_diffrn_orient_matrix_UB_33      0.0236621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            60906
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.602
_diffrn_reflns_theta_min         2.733
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark black'
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_description       prism
_exptl_crystal_F_000             6176
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     893
_refine_ls_number_reflns         18419
_refine_ls_number_restraints     237
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.2216
_refine_ls_R_factor_gt           0.1290
_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^)+(0.0021P)^2^+73.2340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2360
_refine_ls_wR_factor_ref         0.2710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6273
_reflns_number_total             18419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ee02467b2.cif
_cod_data_source_block           tx151183_auto_sq
_cod_original_cell_volume        18825.9(19)
_cod_database_code               1572792
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     CHClFNOS
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.389
_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. Restrained distances
 C46-C45 = C51-C46 = C51-C52 = C47-C46 = C48-C47 = C49-C48 = C78-C77 = C78-C81
 = C78-C79 = C79-C80 = C54-C53 = C54-C55 = C56-C55 = C57-C56 = C58-C57 = C59-
 C54 = C59-C60 = C61-C60 = C62-C61 = C63-C62 = C66-C65 = C73-C66 = C73-C74 =
 C74-C75 = C76-C75 = C66-C67 = C68-C67 = C69-C68 = C70-C69 = C71-C70
 1.54 with sigma of 0.01
 C63-C64
 1.54 with sigma of 0.01
 C49-C50
 1.54 with sigma of 0.01
 C71-C72
 1.54 with sigma of 0.01
 C8-C7 = C6-C7 = C5-C6 = C4-C5 = C4-C3 = C3-C8
 1.39 with sigma of 0.01
 N3-C53
 1.45 with sigma of 0.01
 C80-C78
 2.5 with sigma of 0.02
 C62-C64
 2.5 with sigma of 0.02
 C61-C63
 2.5 with sigma of 0.02
 C74-C76
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C78, C79, C80
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C63, C62
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C57, C58
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73 \\sim
C74 \\sim C75 \\sim C76: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.7A
C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 1.7A
C54 \\sim C55 \\sim C56 \\sim C57 \\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim
C62 \\sim C63 \\sim C63 \\sim C64: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 1.7A
C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50 \\sim C51 \\sim C52:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
5. Others
 Fixed Z: C78(0.447829)
6.a Riding coordinates:
 C50(H50A,H50B,H50C), C64(H64A,H64B,H64C), C72(H72A,H72B,H72C), C76(H76A,H76B,
 H76C)
6.b Ternary CH refined with riding coordinates:
 C46(H46), C54(H54), C66(H66), C78(H78)
6.c Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C51(H51A,
 H51B), C53(H53A,H53B), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B),
 C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B),
  C65(H65A,H65B), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,
 H70B), C71(H71A,H71B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B),
 C77(H77A,H77B), C79(H79A,H79B)
6.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C13(H13), C32(H32), C36(H36), C39(H39)
6.e Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C58(H58A,H58B,H58C)
;
_shelx_res_checksum              9461
_shelx_fab_checksum              94273
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.744
_oxdiff_exptl_absorpt_empirical_full_min 0.451