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_1572793
_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         'C84 H86 Cl4 F N6 O2 S4, 0.125[], 0.125[]'
_chemical_formula_sum            'C84 H88 Cl4 F N6 O2 S4'
_chemical_formula_weight         1502.64
_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.cc2jbcv3
_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                 107.330(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.4208(12)
_cell_length_b                   23.6514(17)
_cell_length_c                   33.9562(15)
_cell_measurement_reflns_used    7607
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.6900
_cell_measurement_theta_min      2.6400
_cell_volume                     18722.3(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      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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    -14.00  19.00   0.50    4.00    --  -46.41  35.00-150.00   66
  2  \w   -120.00 -32.00   0.50    4.00    --  -46.41 -35.00  52.00  176
  3  \w     37.00 108.00   0.50    4.00    --   46.41  35.00-150.00  142
  4  \w    -17.00   9.00   0.50    4.00    --   46.41 -35.00  52.00   52
  5  \w   -171.00 -98.00   0.50   20.00    -- -104.50 -35.00  52.00  146
  6  \w    146.00 175.00   0.50   20.00    --  108.85  35.00-150.00   58
  7  \w    -39.00  22.00   0.50    4.00    --  -46.41  38.00   0.00  122
  8  \w    -21.00  28.00   0.50    4.00    --  -46.41  19.00-180.00   98
  9  \w   -104.00 -78.00   0.50   20.00    -- -104.50 125.00-150.00   52
 10  \w    -67.00 -31.00   0.50   20.00    -- -104.50  61.00   0.00   72
 11  \w    -63.00 -35.00   0.50   20.00    -- -104.50 125.00-150.00   56
 12  \w    -67.00 -31.00   0.50   20.00    -- -104.50  61.00-150.00   72
 13  \w    -67.00 -39.00   0.50   20.00    -- -104.50  61.00-180.00   56
 14  \w    -66.00 -32.00   0.50   20.00    -- -104.50  61.00 -60.00   68
 15  \w   -101.00 -33.00   0.50   20.00    -- -104.50  77.00 120.00  136
 16  \w    -66.00 -32.00   0.50   20.00    -- -104.50  61.00-120.00   68
 17  \w    -68.00 -43.00   0.50   20.00    -- -104.50  61.00  60.00   50
 18  \w    -62.00 -35.00   0.50   20.00    -- -104.50  61.00 -30.00   54
 19  \w    -66.00 -32.00   0.50   20.00    -- -104.50  61.00  30.00   68
 20  \w     83.00 109.00   0.50   20.00    --  108.85 -77.00-150.00   52
 21  \w     39.00  66.00   0.50   20.00    --  108.85 -77.00-150.00   54
 22  \w     36.00  75.00   0.50   20.00    --  108.85 -61.00  60.00   78
 23  \w    150.00 176.00   0.50   20.00    --  108.85 125.00  60.00   52
 24  \w     60.00 108.00   0.50   20.00    --  108.85 -77.00  90.00   96
 25  \w     41.00  66.00   0.50   20.00    --  108.85 -61.00 150.00   50
 26  \w     81.00 111.00   0.50   20.00    --  108.85 125.00  60.00   60
 27  \w     36.00  61.00   0.50   20.00    --  108.85 -61.00 -90.00   50
 28  \w    118.00 165.00   0.50   20.00    --  108.85  15.00 -30.00   94
 29  \w     40.00  72.00   0.50   20.00    --  108.85 -61.00  30.00   64
;
_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      -0.0428468000
_diffrn_orient_matrix_UB_12      -0.0191014000
_diffrn_orient_matrix_UB_13      -0.0410987000
_diffrn_orient_matrix_UB_21      0.0409164000
_diffrn_orient_matrix_UB_22      0.0219232000
_diffrn_orient_matrix_UB_23      -0.0234575000
_diffrn_orient_matrix_UB_31      0.0294451000
_diffrn_orient_matrix_UB_32      -0.0581811000
_diffrn_orient_matrix_UB_33      0.0045859000
_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  0.0695
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            60711
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.998
_diffrn_reflns_theta_min         2.661
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09340
_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            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_description       prism
_exptl_crystal_F_000             6328
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         16839
_refine_ls_number_restraints     240
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.2094
_refine_ls_R_factor_gt           0.1256
_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^)+(0.0014P)^2^+95.7560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2311
_refine_ls_wR_factor_ref         0.2651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6582
_reflns_number_total             16839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ee02467b2.cif
_cod_data_source_block           tx14797_auto_sq
_cod_database_code               1572793
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOFClS
_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
 C47-C46 = C48-C47 = C49-C48 = C51-C50 = C52-C51 = C53-C52 = C55-C54 = C62-C55
 = C63-C62 = C64-C63 = C65-C64 = C56-C55 = C57-C56 = C58-C57 = C59-C58 = C60-
 C59 = C61-C60 = C50-C47 = C68-C67 = C69-C68 = C70-C69 = C71-C70 = C72-C71 =
 C73-C67 = C74-C73 = C75-C74 = C76-C75 = C78-C77 = C81-C78 = C82-C81 = C83-C82 =
  C84-C83 = C79-C78 = C80-C79
 1.54 with sigma of 0.01
 H66A-H54A
 2.1 with sigma of 0.01
 C47-C49
 2.5 with sigma of 0.02
 C46-C50
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C50, C47
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C50, C51
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C52, C53
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C71, C72
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C75, C76
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50 \\sim C51 \\sim C52 \\sim C53:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C55 \\sim C56 \\sim C57 \\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim
C63 \\sim C64 \\sim C65: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81 \\sim C82 \\sim C83 \\sim C84:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
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 0.02 and sigma for terminal atoms of
0.04 within 1.7A
5. Others
 Fixed U22: F1(0.29315)
6.a Riding coordinates:
 C49(H49A,H49B,H49C), C53(H53A,H53B,H53C), C61(H61A,H61B,H61C), C65(H65A,H65B,
 H65C), C76(H76A,H76B,H76C), C80(H80A,H80B,H80C), C84(H84A,H84B,H84C)
6.b Ternary CH refined with riding coordinates:
 C47(H47), C55(H55), C67(H67), C78(H78)
6.c Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C48(H48A,H48B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,
 H52B), C54(H54A,H54B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B),
 C59(H59A,H59B), C60(H60A,H60B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B),
  C66(H66A,H66B), 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), C81(H81A,H81B), C82(H82A,H82B), C83(H83A,H83B)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C13(H13), C33(H33), C37(H37), C40(H40)
6.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              79669
_shelx_fab_checksum              70728
_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 5.043
_oxdiff_exptl_absorpt_empirical_full_min 0.427