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_1575637
_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 H90 Cl2 F4 N8 O2 S4'
_chemical_formula_sum            'C86 H90 Cl2 F4 N8 O2 S4'
_chemical_formula_weight         1542.79
_chemical_name_systematic        QX-2Cl
_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             2024-11-27
_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                 106.033(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.133(2)
_cell_length_b                   23.5227(19)
_cell_length_c                   32.585(3)
_cell_measurement_reflns_used    9726
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      24.24
_cell_measurement_theta_min      2.42
_cell_volume                     17778(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-4 (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 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       '\w and \f 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  0.1011
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            219818
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_min         2.093
_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    0.223
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0794 after correction.
The Ratio of minimum to maximum transmission is 0.9159.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             6496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.00107(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     960
_refine_ls_number_reflns         16270
_refine_ls_number_restraints     809
_refine_ls_restrained_S_all      1.320
_refine_ls_R_factor_all          0.2128
_refine_ls_R_factor_gt           0.1475
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+120.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3221
_refine_ls_wR_factor_ref         0.3527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7880
_reflns_number_total             16270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ee04322k2.cif
_cod_data_source_block           b241121d_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_database_code               1575637
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.972
_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
 C8_1-C7_1 = C7_1-C6_1 = C6_1-C5_1 = C5_1-C2_1 = C3_1-C2_1 = C4_1-C3_1 = C2_1-
 C1_1
 C8_2-C7_2 = C7_2-C6_2 = C6_2-C5_2 = C5_2-C2_2 = C3_2-C2_2 = C4_2-C3_2 = C2_2-
 C1_2
 1.5 with sigma of 0.01
 C6_3-C5_3 = C5_3-C4_3 = C4_3-C3_3 = C3_3-C2_3 = C2_3-C1_3 = C7_3-C2_3 = C8_3-
 C7_3 = C9_3-C8_3 = C9_3-C10_3 = C11_3-C10_3 = C12_3-C11_3
 C6_4-C5_4 = C5_4-C4_4 = C4_4-C3_4 = C3_4-C2_4 = C2_4-C1_4 = C7_4-C2_4 = C8_4-
 C7_4 = C9_4-C8_4 = C9_4-C10_4 = C11_4-C10_4 = C12_4-C11_4
 1.5 with sigma of 0.01
 C6_1-C8_1 = C7_1-C5_1
 C6_2-C8_2 = C7_2-C5_2
 2.5 with sigma of 0.01
 C6_1-C2_1 = C5_1-C3_1
 C6_2-C2_2 = C5_2-C3_2
 2.5 with sigma of 0.01
 C4_1-C2_1 = C3_1-C1_1
 C4_2-C2_2 = C3_2-C1_2
 2.5 with sigma of 0.01
 C1_1-C5_1
 C1_2-C5_2
 2.5 with sigma of 0.01
 C12_3-C10_3 = C9_3-C11_3
 C12_4-C10_4 = C9_4-C11_4
 2.5 with sigma of 0.01
 C10_3-C8_3 = C7_3-C9_3
 C10_4-C8_4 = C7_4-C9_4
 2.5 with sigma of 0.01
 C8_3-C2_3 = C7_3-C3_3
 C8_4-C2_4 = C7_4-C3_4
 2.5 with sigma of 0.01
 C2_3-C4_3 = C3_3-C5_3
 C2_4-C4_4 = C3_4-C5_4
 2.5 with sigma of 0.01
 C4_3-C6_3 = C3_3-C1_3
 C4_4-C6_4 = C3_4-C1_4
 2.5 with sigma of 0.01
 C1_3-C7_3
 C1_4-C7_4
 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
C11_3 \\sim C12_3: within 2A with sigma of 0.006 and sigma for terminal atoms
of 0.012 within 2A
C1_2 \\sim C2_2: within 2A with sigma of 0.006 and sigma for terminal atoms of
0.012 within 2A
C6_2 \\sim C7_2: within 2A with sigma of 0.006 and sigma for terminal atoms of
0.012 within 2A
C7_2 \\sim C8_2: within 2A with sigma of 0.006 and sigma for terminal atoms of
0.012 within 2A
C7_3 \\sim C8_3 \\sim C9_3: within 2A with sigma of 0.006 and sigma for
terminal atoms of 0.012 within 2A
C5_4 \\sim C6_4: within 2A with sigma of 0.006 and sigma for terminal atoms of
0.012 within 2A
C7_3 \\sim C2_3: within 2A with sigma of 0.006 and sigma for terminal atoms of
0.012 within 2A
C1_3 \\sim C2_3: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
C7_1 \\sim C8_1: within 2A with sigma of 0.006 and sigma for terminal atoms of
0.012 within 2A
C3_3 \\sim C4_3: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
C8_4 \\sim C9_4: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
4.a Riding coordinates:
 C1(H1A,H1B), C1(H1A,H1B), C8(H8A,H8B,H8C), C11(H11A,H11B), C12(H12A,H12B,
 H12C), C6(H6A,H6B,H6C), C11(H11A,H11B), C12(H12A,H12B,H12C)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C2(H2), C2(H2), C2(H2)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C3(H3A,H3B), C5(H5A,H5B),
 C6(H6A,H6B), C7(H7A,H7B), C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C1(H1A,H1B), C3(H3A,
 H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C13(H13), C34(H34), C38(H38), C41(H41)
4.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              98933
_shelx_fab_checksum              72558
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU