“Head surgery” of polycyclic o-quinones with cyanated aromatic rings towards high electron mobility acceptors enables 19.6% efficiency in additive-free binary organic solar cells
Duan, Tainan; Wang, Jia; Zuo, Xiaochan; Zhong, Yanyi; Long, Yuhong; Wang, Peiran; Tu, Kaihuai; Zhong, Cheng; Zhang, Jiangbin; Rakitin, Oleg A.; Yao, Zhaoyang; Wan, Xiangjian; Zhao, Yan; Kan, Bin; Chen, Yongsheng; Energy & Environmental Science 18 (2025) 3773–3783; doi:10.1039/D5EE00031A

data_1574096
_publ_section_title
;
 &#x201C;Head surgery&#x201D; of polycyclic o-quinones with cyanated
 aromatic rings towards high electron mobility acceptors enables 19.6%
 efficiency in additive-free binary organic solar cells
;
_journal_issue                   8
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              3773
_journal_page_last               3783
_journal_paper_doi               10.1039/D5EE00031A
_journal_volume                  18
_journal_year                    2025
_chemical_formula_moiety         'C90 H94 Cl4 N8 O2 S5'
_chemical_formula_sum            'C90 H94 Cl4 N8 O2 S5'
_chemical_formula_weight         1621.83
_chemical_name_systematic        CD-2
_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
_audit_creation_date             2025-02-19
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-21 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.957(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.131(5)
_cell_length_b                   22.225(4)
_cell_length_c                   14.008(2)
_cell_measurement_reflns_used    3395
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      62.83
_cell_measurement_theta_min      2.57
_cell_volume                     8411(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX6 V2024.9-0 (Bruker, 2024)'
_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      223.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24569
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        50.434
_diffrn_reflns_theta_max         50.434
_diffrn_reflns_theta_min         2.574
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.851
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1372 before and 0.0754 after correction.
The Ratio of minimum to maximum transmission is 0.7482.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             3416
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.306
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.405
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.1054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3007
_refine_ls_wR_factor_ref         0.3433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2951
_reflns_number_total             4406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ee00031a2.cif
_cod_data_source_block           cu_240919lu_lgpz130690_2_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 1574095--1574096.cif.
;
_cod_original_cell_volume        8412(2)
_cod_database_code               1574096
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.783
_shelx_estimated_absorpt_t_min   0.708
_olex2_refinement_description
;
1. Restrained distances
 C17-C16 = C16-C15 = C17-C18 = C19-C18 = C19-C20 = C20-C21 = C21-C22 = C23-C22
 = C24-C23
 1.5 with sigma of 0.01
 C44-C45 = C44-C43 = C43-C42 = C42-C41 = C40-C41 = C40-C35 = C35-C36 = C37-C36
 = C38-C37 = C38-C39
 1.5 with sigma of 0.01
 C24-C22 = C23-C21
 2.5 with sigma of 0.01
 C22-C20 = C21-C19
 2.5 with sigma of 0.01
 C20-C18 = C19-C17
 2.5 with sigma of 0.01
 C18-C16 = C17-C15
 2.5 with sigma of 0.01
 C37-C39 = C38-C36
 2.5 with sigma of 0.01
 C37-C35 = C40-C36
 2.5 with sigma of 0.01
 C35-C41 = C42-C40
 2.5 with sigma of 0.01
 C41-C43 = C44-C42
 2.5 with sigma of 0.01
 C45-C43
 2.5 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
C34 \\sim C36 \\sim C35 \\sim C37 \\sim C40 \\sim C39 \\sim C38 \\sim C41 \\sim
C42 \\sim C43 \\sim C44 \\sim C45: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C16 \\sim C18 \\sim C17 \\sim C21 \\sim C20 \\sim C19 \\sim C22 \\sim C23 \\sim
C24: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3.a Riding coordinates:
 C34(H34A,H34B)
3.b Ternary CH refined with riding coordinates:
 C35(H35)
3.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C36(H36A,H36B), C41(H41A,H41B), C37(H37A,H37B), C22(H22A,
 H22B), C18(H18A,H18B), C40(H40A,H40B), C17(H17A,H17B), C23(H23A,H23B),
 C21(H21A,H21B), C20(H20A,H20B), C42(H42A,H42B), C19(H19A,H19B), C38(H38A,H38B),
  C43(H43A,H43B), C44(H44A,H44B)
3.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C13(H13)
3.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C39(H39A,H39B,H39C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              30809
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU