“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_1574095
_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         'C96 H98 Cl4 N8 O2 S4, 1[CHCl3], 2[CH3OH]'
_chemical_formula_sum            'C99 H107 Cl7 N8 O4 S4'
_chemical_formula_weight         1849.31
_chemical_name_systematic        CD-1
_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             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                69.159(15)
_cell_angle_beta                 81.645(13)
_cell_angle_gamma                89.253(14)
_cell_formula_units_Z            2
_cell_length_a                   10.5853(18)
_cell_length_b                   21.091(4)
_cell_length_c                   23.544(5)
_cell_measurement_reflns_used    5799
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      76.37
_cell_measurement_theta_min      3.53
_cell_volume                     4856.0(17)
_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  (Sheldrick, 2015)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0797
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            66960
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         4.404
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.05550000000000001
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.094
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1264 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.7583.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.859
_refine_diff_density_min         -1.369
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1031
_refine_ls_number_reflns         17739
_refine_ls_number_restraints     335
_refine_ls_restrained_S_all      1.315
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.1078
_refine_ls_shift/su_max          0.002
_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          0.3004
_refine_ls_wR_factor_ref         0.3403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10769
_reflns_number_total             17739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ee00031a2.cif
_cod_data_source_block           cu_240917lu_lgpz130690_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 1574095--1574096.cif.
;
_cod_original_cell_volume        4856.1(17)
_cod_database_code               1574095
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.768
_shelx_estimated_absorpt_t_min   0.689
_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
 C2_1-C1_1 = C3_1-C2_1 = C4_1-C3_1 = C5_1-C4_1 = C6_1-C5_1 = C7_1-C2_1 = C8_1-
 C7_1 = C9_1-C8_1 = C9_1-C10_1 = C11_1-C10_1 = C12_1-C11_1
 C2_2-C1_2 = C3_2-C2_2 = C4_2-C3_2 = C5_2-C4_2 = C6_2-C5_2 = C7_2-C2_2 = C8_2-
 C7_2 = C9_2-C8_2 = C9_2-C10_2 = C11_2-C10_2 = C12_2-C11_2
 1.5 with sigma of 0.01
 C2_3-C1_3 = C3_3-C2_3 = C4_3-C3_3 = C5_3-C4_3 = C6_3-C5_3 = C7_3-C6_3 = C8_3-
 C7_3 = C9_3-C8_3
 C2_5-C1_5 = C3_5-C2_5 = C4_5-C3_5 = C5_5-C4_5 = C6_5-C5_5 = C7_5-C6_5 = C8_5-
 C7_5 = C9_5-C8_5
 1.5 with sigma of 0.01
 C12_1-C10_1 = C9_1-C11_1
 C12_2-C10_2 = C9_2-C11_2
 2.5 with sigma of 0.01
 C10_1-C8_1 = C7_1-C9_1
 C10_2-C8_2 = C7_2-C9_2
 2.5 with sigma of 0.01
 C8_1-C2_1 = C3_1-C7_1
 C8_2-C2_2 = C3_2-C7_2
 2.5 with sigma of 0.01
 C2_1-C4_1 = C3_1-C5_1
 C2_2-C4_2 = C3_2-C5_2
 2.5 with sigma of 0.01
 C4_1-C6_1
 C4_2-C6_2
 2.5 with sigma of 0.01
 C1_1-C3_1
 C1_2-C3_2
 2.5 with sigma of 0.01
 C1_1-C7_1
 C1_2-C7_2
 2.5 with sigma of 0.01
 C7_3-C9_3 = C8_3-C6_3
 C7_5-C9_5 = C8_5-C6_5
 2.5 with sigma of 0.01
 C7_3-C5_3 = C4_3-C6_3
 C7_5-C5_5 = C4_5-C6_5
 2.5 with sigma of 0.01
 C5_3-C3_3 = C2_3-C4_3
 C5_5-C3_5 = C2_5-C4_5
 2.5 with sigma of 0.01
 C1_3-C3_3
 C1_5-C3_5
 2.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1_1 \\sim C2_1 \\sim C7_1 \\sim C3_1 \\sim C8_1 \\sim C4_1 \\sim C9_1 \\sim
C5_1 \\sim C10_1 \\sim C11_1 \\sim C12_1 \\sim C6_1 \\sim C1_2 \\sim C2_2 \\sim
C7_2 \\sim C3_2 \\sim C8_2 \\sim C4_2 \\sim C9_2 \\sim C5_2 \\sim C10_2 \\sim
C11_2 \\sim C12_2 \\sim C6_2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C9_2 \\sim C10_2 \\sim C11_2: within 2A with sigma of 0.004 and sigma for
terminal atoms of 0.008 within 2A
C6_1 \\sim C5_1: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C5_2 \\sim C6_2: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C11_1 \\sim C12_1: within 2A with sigma of 0.007 and sigma for terminal atoms
of 0.014 within 2A
C10_1 \\sim C11_1: within 2A with sigma of 0.002 and sigma for terminal atoms
of 0.004 within 2A
C11_2 \\sim C12_2: within 2A with sigma of 0.005 and sigma for terminal atoms
of 0.01 within 2A
C2_3 \\sim C3_3 \\sim C4_3 \\sim C7_3 \\sim C6_3 \\sim C8_3 \\sim C9_3 \\sim
C5_3 \\sim C1_3 \\sim C2_5 \\sim C3_5 \\sim C4_5 \\sim C7_5 \\sim C6_5 \\sim
C8_5 \\sim C9_5 \\sim C5_5 \\sim C1_5: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
C3_3 \\sim C4_3 \\sim C5_3 \\sim C6_3: within 2A with sigma of 0.007 and sigma
for terminal atoms of 0.014 within 2A
C29 \\sim C30: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C3_5 \\sim C4_5: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C15 \\sim C1_5: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C2_3 \\sim C3_3: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C8_3 \\sim C9_3: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C2_5 \\sim C3_5: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C1_5 \\sim C2_5: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
4.a Riding coordinates:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C2(H2)
4.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B),
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C1(H1A,H1B), C3(H3A,H3B),
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C13(H13), C28(H28), C29(H29), C30(H30), C31(H31), C42(H42),
 C46(H46), C49(H49)
4.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9(H9A,H9B,H9C), C6(H6A,H6B,H6C), C12(H12A,H12B,H12C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 191 electrons were 
found in a volume of 824\%A^3^ in 3 voids per unit cell. 
This is consistent with the presence of 
1[CHCl3], 2[CH3OH] per formula unit 
which account for 188 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              50194
_shelx_fab_checksum              9806
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU