Dispersion effect of chlorination-induced intermolecular stacking optimization of small-molecule acceptors for high-performance organic solar cells
Hu, Kewei; Ge, Yu; Yang, Hang; Xu, Yue; Qian, Jiahao; Zhu, Xuncheng; Wu, Yue; Cui, Chaohua; Li, Yongfang; Energy & Environmental Science 18 (2025) 9194–9204; doi:10.1039/D5EE04322K

data_1575635
_publ_section_title
;
 Dispersion effect of chlorination-induced intermolecular stacking
 optimization of small-molecule acceptors for high-performance organic
 solar cells
;
_journal_issue                   20
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              9194
_journal_page_last               9204
_journal_paper_doi               10.1039/D5EE04322K
_journal_volume                  18
_journal_year                    2025
_chemical_formula_moiety         'C86 H91 Cl F4 N8 O2 S4'
_chemical_formula_sum            'C86 H91 Cl F4 N8 O2 S4'
_chemical_formula_weight         1508.35
_chemical_name_systematic        QX-Cl
_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_creation_date             2024-10-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-16 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.79(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.281(18)
_cell_length_b                   23.137(15)
_cell_length_c                   32.47(2)
_cell_measurement_reflns_used    8305
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.44
_cell_volume                     17464(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      223.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS 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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1376
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            170729
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.981
_diffrn_source                   TXS
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1438 before and 0.0835 after correction.
The Ratio of minimum to maximum transmission is 0.9202.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             6368
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     963
_refine_ls_number_reflns         15389
_refine_ls_number_restraints     326
_refine_ls_restrained_S_all      1.274
_refine_ls_R_factor_all          0.2365
_refine_ls_R_factor_gt           0.1459
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+150.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3053
_refine_ls_wR_factor_ref         0.3449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6445
_reflns_number_total             15389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ee04322k2.cif
_cod_data_source_block           b240927c_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 1575635--1575637.cif.
;
_cod_original_cell_volume        17462(22)
_cod_database_code               1575635
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.977
_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-C2_3 = C6_3-C5_3 = C7_3-C6_3 = C8_3-
 C7_3
 C2_4-C1_4 = C3_4-C2_4 = C4_4-C3_4 = C5_4-C2_4 = C6_4-C5_4 = C7_4-C6_4 = C8_4-
 C7_4
 1.5 with sigma of 0.01
 C4_1-C6_1 = C3_1-C5_1 = C4_1-C2_1 = C7_1-C3_1 = C2_1-C8_1 = C7_1-C9_1 = C8_1-
 C10_1 = C9_1-C11_1 = C10_1-C12_1 = C1_1-C7_1 = C1_1-C3_1
 C4_2-C6_2 = C3_2-C5_2 = C4_2-C2_2 = C7_2-C3_2 = C2_2-C8_2 = C7_2-C9_2 = C8_2-
 C10_2 = C9_2-C11_2 = C10_2-C12_2 = C1_2-C7_2 = C1_2-C3_2
 2.5 with sigma of 0.01
 C4_3-C2_3 = C3_3-C5_3 = C3_3-C1_3 = C2_3-C6_3 = C5_3-C7_3 = C6_3-C8_3 = C1_3-
 C5_3
 C4_4-C2_4 = C3_4-C5_4 = C3_4-C1_4 = C2_4-C6_4 = C5_4-C7_4 = C6_4-C8_4 = C1_4-
 C5_4
 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 C4_1 \\sim C8_1 \\sim C9_1 \\sim
C5_1 \\sim C6_1 \\sim C12_1 \\sim C11_1 \\sim C10_1 \\sim C1_2 \\sim C2_2 \\sim
C7_2 \\sim C3_2 \\sim C4_2 \\sim C8_2 \\sim C9_2 \\sim C5_2 \\sim C6_2 \\sim
C12_2 \\sim C11_2 \\sim C10_2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C1_3 \\sim C2_3 \\sim C5_3 \\sim C6_3 \\sim C3_3 \\sim C7_3 \\sim C8_3 \\sim
C4_3 \\sim C1_4 \\sim C2_4 \\sim C5_4 \\sim C6_4 \\sim C3_4 \\sim C7_4 \\sim
C8_4 \\sim C4_4: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C4_1 \\sim C5_1: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C1_2 \\sim C2_2: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C7_2 \\sim C8_2: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C6_3 \\sim C7_3: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C6_4 \\sim C7_4: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C32 \\sim C1_2: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C1_3 \\sim N4: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C3_2 \\sim C4_2: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C8_4 \\sim C7_4: 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
C8_2 \\sim C9_2: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C11_2 \\sim C12_2 \\sim C10_2: within 2A with sigma of 0.007 and sigma for
terminal atoms of 0.014 within 2A
4. Others
 Sof(Cl1A)=Sof(H27)=1-FVAR(1)
 Sof(Cl1)=Sof(H26)=FVAR(1)
5.a Riding coordinates:
 C6(H6A,H6B,H6C), C1(H1A,H1B)
5.b Ternary CH refined with riding coordinates:
 C2(H2), C2(H2), C2(H2), C2(H2)
5.c Secondary CH2 refined with riding coordinates:
 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), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C1(H1A,
 H1B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C13(H13), C26(H26), C27(H27), C34(H34), C38(H38), C41(H41)
5.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C12(H12A,H12B,H12C), C4(H4A,H4B,H4C),
 C8(H8A,H8B,H8C), C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              74659
_shelx_fab_checksum              37670
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU