Fine-tuning central extended unit symmetry via atom-level asymmetric molecular design enables efficient binary organic solar cells
Liu, Jian; Wang, Ruohan; Li, Longyu; Zhao, Wenkai; Suo, Zhaochen; Shi, Wendi; Long, Guankui; Yao, Zhaoyang; Wan, Xiangjian; Chen, Yongsheng; Energy & Environmental Science 18 (2025) 4470–4479; doi:10.1039/D4EE06155A

data_1574295
_publ_section_title
;
 Fine-tuning central extended unit symmetry via atom-level asymmetric
 molecular design enables efficient binary organic solar cells
;
_journal_issue                   9
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              4470
_journal_page_last               4479
_journal_paper_doi               10.1039/D4EE06155A
_journal_volume                  18
_journal_year                    2025
_chemical_formula_moiety         'C126 H155 F4 N9 O2 S4'
_chemical_formula_sum            'C126 H155 F4 N9 O2 S4'
_chemical_formula_weight         2031.82
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-03 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                104.389(9)
_cell_angle_beta                 108.549(9)
_cell_angle_gamma                92.542(9)
_cell_formula_units_Z            2
_cell_length_a                   17.182(3)
_cell_length_b                   19.052(4)
_cell_length_c                   19.726(4)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      55.18
_cell_measurement_theta_min      3.17
_cell_volume                     5876(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (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  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE MetalJet PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            63726
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.907
_diffrn_reflns_theta_min         2.139
_diffrn_source                   MetalJet
_diffrn_source_current           2.85
_diffrn_source_power             0.1986735
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1494 before and 0.0779 after correction.
The Ratio of minimum to maximum transmission is 0.6768.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_description       block
_exptl_crystal_F_000             2180
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1308
_refine_ls_number_reflns         21015
_refine_ls_number_restraints     534
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1953
_refine_ls_R_factor_gt           0.1323
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+13.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3177
_refine_ls_wR_factor_ref         0.3508
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9952
_reflns_number_total             21015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ee06155a2.cif
_cod_data_source_block           240517lulgpz143782_1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1574295--1574296.cif.
;
_cod_database_code               1574295
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.912
_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
 C90-C89 = C88-C89 = C88-C87 = C87-C86 = C86-C85 = C85-C84 = C84-C83 = C82-C83
 = C82-C81 = C81-C80 = C91-C80 = C92-C91 = C93-C92 = C94-C93 = C95-C94 = C96-
 C95 = C97-C96 = C98-C97 = C98-C99 = C100-C99 = C100-C101 = C101-C102
 1.5 with sigma of 0.01
 C64-C65 = C63-C64 = C62-C63 = C62-C61 = C61-C60 = C60-C59 = C59-C58 = C58-C57
 = C57-C56 = C56-C55 = C55-C15
 1.5 with sigma of 0.01
 C126-C125 = C124-C125 = C123-C124 = C123-C122 = C121-C122 = C121-C120 = C120-
 C119 = C119-C118 = C118-C117 = C117-C104 = C105-C104 = C106-C105 = C107-C106 =
 C108-C107 = C109-C108 = C109-C110 = C111-C110 = C111-C112 = C113-C112 = C114-
 C113 = C114-C115 = C116-C115
 1.5 with sigma of 0.01
 C52-C51 = C50-C51 = C49-C50 = C49-C48 = C47-C48 = C47-C46 = C46-C45 = C45-C44
 = C44-C43 = C43-C28
 1.5 with sigma of 0.01
 C63-C65
 2.5 with sigma of 0.01
 C88-C86
 2.5 with sigma of 0.01
 C90-C88
 2.5 with sigma of 0.01
 C100-C102
 2.5 with sigma of 0.01
 C86-C84
 2.5 with sigma of 0.01
 C101-C99
 2.5 with sigma of 0.01
 C87-C89
 2.5 with sigma of 0.01
 C100-C98
 2.5 with sigma of 0.01
 C85-C87
 2.5 with sigma of 0.01
 C99-C97
 2.5 with sigma of 0.01
 C96-C98
 2.5 with sigma of 0.01
 C120-C122
 2.5 with sigma of 0.01
 C126-C124
 2.5 with sigma of 0.01
 C121-C119
 2.5 with sigma of 0.01
 C124-C122
 2.5 with sigma of 0.01
 C113-C115
 2.5 with sigma of 0.01
 C108-C110
 2.5 with sigma of 0.01
 C112-C114
 2.5 with sigma of 0.01
 C125-C123
 2.5 with sigma of 0.01
 C113-C111
 2.5 with sigma of 0.01
 C123-C121
 2.5 with sigma of 0.01
 C110-C112
 2.5 with sigma of 0.01
 C111-C109
 2.5 with sigma of 0.01
 C120-C118
 2.5 with sigma of 0.01
 C116-C114
 2.5 with sigma of 0.01
 C59-C61
 2.5 with sigma of 0.01
 C59-C57
 2.5 with sigma of 0.01
 C62-C60
 2.5 with sigma of 0.01
 C60-C58
 2.5 with sigma of 0.01
 C64-C62
 2.5 with sigma of 0.01
 C58-C56
 2.5 with sigma of 0.01
 C61-C63
 2.5 with sigma of 0.01
 C46-C48
 2.5 with sigma of 0.01
 C49-C47
 2.5 with sigma of 0.01
 C50-C48
 2.5 with sigma of 0.01
 C47-C45
 2.5 with sigma of 0.01
 C43-C45
 2.5 with sigma of 0.01
 C46-C44
 2.5 with sigma of 0.01
 C50-C52
 2.5 with sigma of 0.01
 C51-C49
 2.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C55 \\sim C56 \\sim C57 \\sim C58 \\sim C59 \\sim C65 \\sim C60 \\sim C64 \\sim
C63 \\sim C62 \\sim C61: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C104 \\sim C105 \\sim C106 \\sim C117 \\sim C118 \\sim C119 \\sim C120 \\sim
C122 \\sim C121 \\sim C124 \\sim C125 \\sim C123 \\sim C126 \\sim C103 \\sim
C107 \\sim C108 \\sim C110 \\sim C109 \\sim C111 \\sim C112 \\sim C113 \\sim
C114 \\sim C115 \\sim C116: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C49 \\sim C50 \\sim C48 \\sim
C52 \\sim C51: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C80 \\sim C81 \\sim C91 \\sim C83 \\sim C82 \\sim C92 \\sim C93 \\sim C94 \\sim
C95 \\sim C84 \\sim C96 \\sim C97 \\sim C98 \\sim C99 \\sim C101 \\sim C100
\\sim C102 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89 \\sim C90: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C125 \\sim C126: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C46 \\sim C47: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C51 \\sim C52: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C58 \\sim C59: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C70 \\sim C71: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C120 \\sim C121: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C47 \\sim C48 \\sim C49 \\sim C50: within 2A with sigma of 0.007 and sigma for
terminal atoms of 0.014 within 2A
C59 \\sim C60: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C64 \\sim C65: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C96 \\sim C97 \\sim C98 \\sim C99 \\sim C100 \\sim C101 \\sim C102: within 2A
with sigma of 0.007 and sigma for terminal atoms of 0.014 within 2A
C120 \\sim C121 \\sim C122: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
4.a Riding coordinates:
 C115(H11Q,H11R), C59(H59A,H59B), C90(H90A,H90B,H90C), C102(H10Q,H10R,H10S),
 C65(H65A,H65B,H65C), C125(H12I,H12J), C52(H52A,H52B,H52C)
4.b Ternary CH refined with riding coordinates:
 C104(H104), C80(H80)
4.c Secondary CH2 refined with riding coordinates:
 C103(H10A,H10B), C79(H79A,H79B), C105(H10C,H10D), C43(H43A,H43B), C106(H10E,
 H10F), C55(H55A,H55B), C56(H56A,H56B), C117(H11A,H11B), C44(H44A,H44B),
 C81(H81A,H81B), C118(H11C,H11D), C107(H10G,H10H), C91(H91A,H91B), C57(H57A,
 H57B), C83(H83A,H83B), C82(H82A,H82B), C92(H92A,H92B), C108(H10I,H10J),
 C119(H11E,H11F), C93(H93A,H93B), C45(H45A,H45B), C94(H94A,H94B), C95(H95A,
 H95B), C84(H84A,H84B), C96(H96A,H96B), C120(H12A,H12B), C110(H11G,H11H),
 C58(H58A,H58B), C109(H10K,H10L), C111(H11I,H11J), C112(H11K,H11L), C46(H46A,
 H46B), C113(H11M,H11N), C114(H11O,H11P), C97(H97A,H97B), C47(H47A,H47B),
 C122(H12C,H12D), C85(H85A,H85B), C98(H98A,H98B), C86(H86A,H86B), C87(H87A,
 H87B), C49(H49A,H49B), C121(H12E,H12F), C88(H88A,H88B), C99(H99A,H99B),
 C89(H89A,H89B), C101(H10M,H10N), C100(H10O,H10P), C124(H12G,H12H), C123(H12K,
 H12L), C60(H60A,H60B), C64(H64A,H64B), C63(H63A,H63B), C62(H62A,H62B),
 C61(H61A,H61B), C50(H50A,H50B), C48(H48A,H48B), C51(H51A,H51B)
4.d Aromatic/amide H refined with riding coordinates:
 C30(H30), C78(H78), C70(H70), C13(H13), C3(H3), C77(H77), C35(H35), C76(H76),
 C38(H38), C9(H9), C73(H73), C72(H72), C71(H71)
4.e Idealised Me refined as rotating group:
 C116(H11S,H11T,H11U), C126(H12M,H12N,H12O)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              10864
_shelx_fab_checksum              79052
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU