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_1574296
_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         'C127 H156 Br F4 N9 O2 S4'
_chemical_formula_sum            'C127 H156 Br F4 N9 O2 S4'
_chemical_formula_weight         2124.75
_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             2024-05-18
_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                104.767(8)
_cell_angle_beta                 108.463(9)
_cell_angle_gamma                91.368(8)
_cell_formula_units_Z            2
_cell_length_a                   17.430(5)
_cell_length_b                   18.929(5)
_cell_length_c                   19.665(5)
_cell_measurement_reflns_used    8287
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      49.11
_cell_measurement_theta_min      3.13
_cell_volume                     5912(3)
_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  (Sheldrick, 2015)'
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.1370
_diffrn_reflns_av_unetI/netI     0.1682
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_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       -19
_diffrn_reflns_number            57113
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        52.981
_diffrn_reflns_theta_max         52.981
_diffrn_reflns_theta_min         2.144
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1385 before and 0.0818 after correction.
The Ratio of minimum to maximum transmission is 0.6783.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       block
_exptl_crystal_F_000             2264
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1312
_refine_ls_number_reflns         20251
_refine_ls_number_restraints     1169
_refine_ls_restrained_S_all      1.293
_refine_ls_R_factor_all          0.2932
_refine_ls_R_factor_gt           0.1554
_refine_ls_shift/su_max          0.058
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3485
_refine_ls_wR_factor_ref         0.4025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6093
_reflns_number_total             20251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ee06155a2.cif
_cod_data_source_block           240517lulgpz143782_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               1574296
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.884
_olex2_refinement_description
;
1. Shared sites
{C127, N01X}
{N9, C00Q}
2. Restrained distances
 C80-C79 = C78-C79 = C77-C78 = C77-C76 = C75-C76 = C75-C74 = C74-C73 = C73-C72
 = C71-C72 = C71-C70 = C69-C70 = C69-C68 = C81-C68 = C82-C81 = C83-C82 = C84-
 C83 = C84-C85 = C85-C86 = C87-C86 = C87-C88 = C89-C88 = C90-C89
 1.5 with sigma of 0.01
 C64-C63 = C62-C63 = C62-C61 = C60-C61 = C60-C59 = C59-C58 = C58-C57 = C57-C56
 = C56-C55 = C55-C54 = C54-C13
 1.5 with sigma of 0.01
 C113-C114 = C113-C112 = C111-C112 = C111-C110 = C110-C109 = C108-C109 = C108-
 C107 = C106-C107 = C106-C105 = C104-C105 = C104-C103 = C103-C92
 1.5 with sigma of 0.01
 C101-C102 = C101-C100 = C100-C99 = C98-C99 = C98-C97 = C96-C97 = C96-C95 =
 C94-C93 = C93-C92
 1.5 with sigma of 0.01
 C94-C95
 1.5 with sigma of 0.01
 C41-C26 = C42-C41 = C43-C42 = C44-C43 = C45-C44 = C46-C45 = C47-C46 = C48-C47
 = C48-C49 = C49-C50 = C51-C50
 1.5 with sigma of 0.01
 C62-C64
 2.5 with sigma of 0.01
 C78-C80
 2.5 with sigma of 0.01
 C60-C62
 2.5 with sigma of 0.01
 C88-C90
 2.5 with sigma of 0.01
 C76-C78
 2.5 with sigma of 0.01
 C109-C107
 2.5 with sigma of 0.01
 C100-C102
 2.5 with sigma of 0.01
 C111-C109
 2.5 with sigma of 0.01
 C105-C103
 2.5 with sigma of 0.01
 C107-C105
 2.5 with sigma of 0.01
 C98-C100
 2.5 with sigma of 0.01
 C113-C111
 2.5 with sigma of 0.01
 C99-C97
 2.5 with sigma of 0.01
 C110-C112
 2.5 with sigma of 0.01
 C101-C99
 2.5 with sigma of 0.01
 C108-C110
 2.5 with sigma of 0.01
 C97-C95
 2.5 with sigma of 0.01
 C106-C108
 2.5 with sigma of 0.01
 C94-C96
 2.5 with sigma of 0.01
 C104-C106
 2.5 with sigma of 0.01
 C95-C93
 2.5 with sigma of 0.01
 C94-C104
 2.5 with sigma of 0.01
 C92-C94
 2.5 with sigma of 0.01
 C96-C98
 2.5 with sigma of 0.01
 C112-C114
 2.5 with sigma of 0.01
 C68-C82
 2.5 with sigma of 0.01
 C84-C86
 2.5 with sigma of 0.01
 C79-C77
 2.5 with sigma of 0.01
 C82-C84
 2.5 with sigma of 0.01
 C77-C75
 2.5 with sigma of 0.01
 C86-C88
 2.5 with sigma of 0.01
 C74-C76
 2.5 with sigma of 0.01
 C81-C83
 2.5 with sigma of 0.01
 C72-C74
 2.5 with sigma of 0.01
 C83-C85
 2.5 with sigma of 0.01
 C73-C71
 2.5 with sigma of 0.01
 C85-C87
 2.5 with sigma of 0.01
 C70-C72
 2.5 with sigma of 0.01
 C87-C89
 2.5 with sigma of 0.01
 C71-C69
 2.5 with sigma of 0.01
 C75-C73
 2.5 with sigma of 0.01
 C68-C70
 2.5 with sigma of 0.01
 C81-C69
 2.5 with sigma of 0.01
 C44-C42
 2.5 with sigma of 0.01
 C49-C51
 2.5 with sigma of 0.01
 C42-C26
 2.5 with sigma of 0.01
 C50-C48
 2.5 with sigma of 0.01
 C43-C45
 2.5 with sigma of 0.01
 C47-C49
 2.5 with sigma of 0.01
 C43-C41
 2.5 with sigma of 0.01
 C48-C46
 2.5 with sigma of 0.01
 C45-C47
 2.5 with sigma of 0.01
 C46-C44
 2.5 with sigma of 0.01
 C61-C59
 2.5 with sigma of 0.01
 C58-C56
 2.5 with sigma of 0.01
 C54-C56
 2.5 with sigma of 0.01
 C59-C57
 2.5 with sigma of 0.01
 C57-C55
 2.5 with sigma of 0.01
 C60-C58
 2.5 with sigma of 0.01
 C63-C61
 2.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
C44 \\sim C45 \\sim C46: within 2A with sigma of 0.007 and sigma for terminal
atoms of 0.014 within 2A
C57 \\sim C58: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C68 \\sim C81: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C73 \\sim C74 \\sim C75: within 2A with sigma of 0.007 and sigma for terminal
atoms of 0.014 within 2A
C82 \\sim C83 \\sim C84 \\sim C85: within 2A with sigma of 0.007 and sigma for
terminal atoms of 0.014 within 2A
C91 \\sim C92 \\sim C93 \\sim C94: within 2A with sigma of 0.007 and sigma for
terminal atoms of 0.014 within 2A
C104 \\sim C105: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
Uanis(C127) = Uanis(N01X)
Uanis(N9) = Uanis(C00Q)
4. Others
 Sof(Br1A)=Sof(H126)=Sof(N01X)=Sof(C00Q)=Sof(H00Q)=1-FVAR(1)
 Sof(Br1)=Sof(N9)=Sof(H123)=Sof(C127)=Sof(H127)=FVAR(1)
 Fixed Z: C78(0.865201) C62(0.79515)
5.a Riding coordinates:
 C103(H10A,H10B), C94(H94A,H94B), C90(H90A,H90B,H90C), C64(H64A,H64B,H64C)
5.b Ternary CH refined with riding coordinates:
 C92(H92), C68(H68)
5.c Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C67(H67A,H67B), C42(H42A,H42B), C54(H54A,H54B), C91(H91A,
 H91B), C93(H93A,H93B), C55(H55A,H55B), C70(H70A,H70B), C56(H56A,H56B),
 C69(H69A,H69B), C81(H81A,H81B), C43(H43A,H43B), C105(H10C,H10D), C72(H72A,
 H72B), C104(H10E,H10F), C71(H71A,H71B), C95(H95A,H95B), C44(H44A,H44B),
 C57(H57A,H57B), C73(H73A,H73B), C107(H10G,H10H), C82(H82A,H82B), C109(H10I,
 H10J), C106(H10K,H10L), C83(H83A,H83B), C99(H99A,H99B), C108(H10M,H10N),
 C45(H45A,H45B), C48(H48A,H48B), C74(H74A,H74B), C61(H61A,H61B), C75(H75A,H75B),
  C60(H60A,H60B), C78(H78A,H78B), C110(H11A,H11B), C111(H11C,H11D), C113(H11E,
 H11F), C96(H96A,H96B), C112(H11J,H11K), C97(H97A,H97B), C98(H98A,H98B),
 C101(H10O,H10P), C100(H10Q,H10R), C79(H79A,H79B), C84(H84A,H84B), C77(H77A,
 H77B), C87(H87A,H87B), C86(H86A,H86B), C88(H88A,H88B), C89(H89A,H89B),
 C85(H85A,H85B), C76(H76A,H76B), C50(H50A,H50B), C46(H46A,H46B), C47(H47A,H47B),
  C49(H49A,H49B), C58(H58A,H58B), C63(H63A,H63B), C59(H59A,H59B), C62(H62A,H62B)
5.d Aromatic/amide H refined with riding coordinates:
 C65(H65), C2(H2), C11(H11), C33(H33), C36(H36), C125(H125), C124(H124),
 C123(H123), C127(H127), C28(H28), C126(H126), C121(H121), C122(H122),
 C00Q(H00Q)
5.e Fitted hexagon refined as free rotating group:
 C4(C65,C66,C1,C2,C3), C33(C32,C31,C36,C35,C34)
5.f Idealised Me refined as rotating group:
 C114(H11G,H11H,H11I), C102(H10S,H10T,H10U), C80(H80A,H80B,H80C), C51(H51A,
 H51B,H51C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              59206
_shelx_fab_checksum              19661
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU