Central Units Hetero Di-Halogenation of Acceptors Enable Organic Solar Cells with 19% Efficiency
Liang, Huazhe; Chen, Hongbin; Zou, Yalu; Zhang, Yunxin; Guo, Yaxiao; Cao, Xiangjian; Bi, Xingqi; Yao, Zhaoyang; Wan, Xiangjian; Chen, Yongsheng; Chemical Communications  (2023) –; doi:10.1039/D3CC04570F

data_7132220
_publ_section_title
;
 Central Units Hetero Di-Halogenation of Acceptors Enable Organic Solar
 Cells with 19% Efficiency
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04570F
_journal_year                    2023
_chemical_formula_moiety         'C104 H120 Br F5 N8 O2 S4'
_chemical_formula_sum            'C104 H120 Br F5 N8 O2 S4'
_chemical_formula_weight         1817.22
_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             2022-11-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                96.957(3)
_cell_angle_beta                 102.674(2)
_cell_angle_gamma                102.055(3)
_cell_formula_units_Z            2
_cell_length_a                   15.5041(10)
_cell_length_b                   17.1702(12)
_cell_length_c                   19.2705(12)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      54.10
_cell_measurement_theta_min      2.83
_cell_volume                     4819.1(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_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 2019/2 (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 0.997
_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  0.0795
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            64080
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.907
_diffrn_reflns_theta_min         2.325
_diffrn_source                   MetalJet
_diffrn_source_current           2.23
_diffrn_source_power             0.1554533
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.240
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0877 before and 0.0574 after correction.
The Ratio of minimum to maximum transmission is 0.8269.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.731
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1120
_refine_ls_number_reflns         17608
_refine_ls_number_restraints     549
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.2030
_refine_ls_R_factor_gt           0.1454
_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^)+(0.0500P)^2^+40.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3259
_refine_ls_wR_factor_ref         0.3514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9492
_reflns_number_total             17608
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04570f2.cif
_cod_data_source_block           221104li_lidz319366_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 
;
_cod_database_code               7132220
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.855
_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. Shared sites
{Br1, F5A}
{F5, Br1A}
3. Restrained distances
 C81-C80 = C82-C81 = C83-C82 = C84-C83 = C85-C84 = C86-C85 = C87-C86 = C88-C87
 = C88-C89 = C90-C89 = C90-C91
 1.5 with sigma of 0.005
 C16-C15 = C17-C16 = C18-C17 = C19-C18 = C20-C19 = C21-C20 = C21-C22 = C22-C23
 = C24-C23 = C25-C24 = C26-C25
 1.5 with sigma of 0.005
 C59-C58 = C57-C58
 1.5 with sigma of 0.005
 C45-C52 = C53-C52 = C54-C53 = C54-C55 = C55-C56 = C57-C56 = C57-C58 = C59-C58
 1.5 with sigma of 0.005
 C45-C46 = C47-C46 = C48-C47 = C48-C49 = C50-C49 = C50-C51
 1.5 with sigma of 0.005
 C61-C70 = C71-C70 = C72-C71 = C73-C72 = C74-C73 = C75-C74
 1.5 with sigma of 0.005
 C62-C61 = C63-C62 = C63-C64 = C65-C64 = C66-C65 = C67-C66 = C68-C67 = C69-C68
 1.5 with sigma of 0.005
 C53-C52
 1.5 with sigma of 0.005
 C45-C52
 1.5 with sigma of 0.005
 C54-C53
 1.5 with sigma of 0.005
 C57-C59
 2.5 with sigma of 0.005
 C24-C26
 2.5 with sigma of 0.005
 C89-C91
 2.5 with sigma of 0.005
 C58-C56
 2.5 with sigma of 0.005
 C48-C50
 2.5 with sigma of 0.005
 C46-C48
 2.5 with sigma of 0.005
 C67-C69
 2.5 with sigma of 0.005
 C70-C72
 2.5 with sigma of 0.005
 C72-C74
 2.5 with sigma of 0.005
 C62-C64
 2.5 with sigma of 0.005
 C61-C71
 2.5 with sigma of 0.005
 C61-C63
 2.5 with sigma of 0.005
 C71-C73
 2.5 with sigma of 0.005
 C64-C66
 2.5 with sigma of 0.005
 C73-C75
 2.5 with sigma of 0.005
 C65-C67
 2.5 with sigma of 0.005
 C63-C65
 2.5 with sigma of 0.005
 C66-C68
 2.5 with sigma of 0.005
 C47-C49
 2.5 with sigma of 0.005
 C45-C47
 2.5 with sigma of 0.005
 C49-C51
 2.5 with sigma of 0.005
 C20-C22
 2.5 with sigma of 0.005
 C22-C24
 2.5 with sigma of 0.005
 C15-C17
 2.5 with sigma of 0.005
 C21-C23
 2.5 with sigma of 0.005
 C23-C25
 2.5 with sigma of 0.005
 C18-C20
 2.5 with sigma of 0.005
 C17-C19
 2.5 with sigma of 0.005
 C21-C19
 2.5 with sigma of 0.005
 C16-C18
 2.5 with sigma of 0.005
 C80-C82
 2.5 with sigma of 0.005
 C86-C88
 2.5 with sigma of 0.005
 C88-C90
 2.5 with sigma of 0.005
 C81-C83
 2.5 with sigma of 0.005
 C82-C84
 2.5 with sigma of 0.005
 C87-C89
 2.5 with sigma of 0.005
 C84-C86
 2.5 with sigma of 0.005
 C83-C85
 2.5 with sigma of 0.005
 C85-C87
 2.5 with sigma of 0.005
 C55-C57
 2.5 with sigma of 0.005
 C54-C56
 2.5 with sigma of 0.005
 C45-C53
 2.5 with sigma of 0.005
 C52-C54
 2.5 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C46 \\sim C52 \\sim C55 \\sim C50 \\sim C53 \\sim C48 \\sim C54 \\sim C51 \\sim
C49 \\sim C47 \\sim C56 \\sim C57 \\sim C58 \\sim C43 \\sim C45 \\sim C59:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C23 \\sim C26 \\sim
C22 \\sim C24 \\sim C25: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
C81 \\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim C86 \\sim C87 \\sim C89 \\sim
C88 \\sim C91 \\sim C90: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
C60 \\sim C70 \\sim C71 \\sim C61 \\sim C72 \\sim C62 \\sim C73 \\sim C64 \\sim
C63 \\sim C65 \\sim C66 \\sim C74 \\sim C68 \\sim C67 \\sim C69 \\sim C75:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
C43 \\sim C45: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
Uanis(C43) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C55)
\\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C48) \\sim Ueq,
Uanis(C45) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C57) \\sim Ueq,
Uanis(C59) \\sim Ueq, Uanis(C58) \\sim Ueq: with sigma of 0.015 and sigma for
terminal atoms of 0.03
Uanis(Br1) = Uanis(F5A)
Uanis(F5) = Uanis(Br1A)
5. Others
 Sof(F5A)=Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=Sof(F5)=FVAR(1)
6.a Riding coordinates:
 C43(H43A,H43B), C60(H60A,H60B), C52(H52A,H52B), C86(H86A,H86B), C21(H21A,
 H21B), C23(H23A,H23B), C26(H26A,H26B,H26C), C48(H48A,H48B), C59(H59A,H59B,
 H59C), C65(H65A,H65B), C66(H66A,H66B), C75(H75A,H75B,H75C), C87(H87A,H87B),
 C89(H89A,H89B), C88(H88A,H88B), C91(H91A,H91B,H91C)
6.b Ternary CH refined with riding coordinates:
 C61(H61), C45(H45)
6.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C70(H70A,H70B), C81(H81A,H81B), C71(H71A,
 H71B), C18(H18A,H18B), C72(H72A,H72B), C82(H82A,H82B), C62(H62A,H62B),
 C19(H19A,H19B), C73(H73A,H73B), C83(H83A,H83B), C46(H46A,H46B), C84(H84A,H84B),
  C20(H20A,H20B), C64(H64A,H64B), C85(H85A,H85B), C55(H55A,H55B), C50(H50A,
 H50B), C53(H53A,H53B), C54(H54A,H54B), C49(H49A,H49B), C47(H47A,H47B),
 C56(H56A,H56B), C57(H57A,H57B), C63(H63A,H63B), C74(H74A,H74B), C68(H68A,H68B),
  C67(H67A,H67B), C58(H58A,H58B), C22(H22A,H22B), C24(H24A,H24B), C25(H25A,
 H25B), C90(H90A,H90B)
6.d Aromatic/amide H refined with riding coordinates:
 C39(H39), C6(H6), C13(H13), C42(H42), C93(H93), C3(H3), C105(H105), C102(H102)
6.e Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C69(H69A,H69B,H69C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              146
_shelx_hkl_checksum              93004
_shelx_fab_checksum              81606
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU