Peripheral halogenation engineering controls molecular stacking to enable highly efficient organic solar cells
Zou, Yalu; Chen, Hongbin; Bi, Xingqi; Xu, Xiaoyun; Wang, Hebin; Lin, Menglu; Ma, Zaifei; Zhang, Mingtao; Li, Chenxi; Wan, Xiangjian; Long, Guankui; Zhaoyang, Yao; Chen, Yongsheng; Energy & Environmental Science 15 (2022) 3519–3533; doi:10.1039/D2EE01340A

data_1567344
_publ_section_title
;
 Peripheral halogenation engineering controls molecular stacking to enable
 highly efficient organic solar cells
;
_journal_issue                   8
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              3519
_journal_page_last               3533
_journal_paper_doi               10.1039/D2EE01340A
_journal_volume                  15
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C104 H120 Cl4 F2 N8 O2 S4'
_chemical_formula_sum            'C104 H120 Cl4 F2 N8 O2 S4'
_chemical_formula_weight         1822.11
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-12-24
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   41.303(4)
_cell_length_b                   41.303(4)
_cell_length_c                   32.517(4)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      50.82
_cell_measurement_theta_min      3.08
_cell_volume                     48040(9)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.14'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON III'
_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  0.1077
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            184279
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.659
_diffrn_reflns_theta_min         2.597
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.414
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1173 before and 0.0779 after correction.
The Ratio of minimum to maximum transmission is 0.6844.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             17388
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.58(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1119
_refine_ls_number_reflns         20892
_refine_ls_number_restraints     733
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1728
_refine_ls_R_factor_gt           0.0932
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1882P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2468
_refine_ls_wR_factor_ref         0.3145
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                8477
_reflns_number_total             20892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ee01340a3.cif
_cod_data_source_block           a
_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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1567342--1567344.cif.
;
_cod_original_cell_volume        48041(11)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               1567344
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.42(4)
 0.58(4)
2. 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
3. Restrained distances
 C57-C55 = C58-C57 = C56-C58 = C59-C56 = C70-C59 = C70-C60 = C69-C60
 1.52 with sigma of 0.002
 C71-C69
 1.52 with sigma of 0.002
 C55-C54
 1.52 with sigma of 0.002
 C4-C27 = C61-C27 = C62-C61 = C63-C62 = C64-C63 = C65-C64 = C66-C65 = C68-C66 =
  C67-C68 = C72-C67
 1.52 with sigma of 0.002
 C72-C73
 1.52 with sigma of 0.002
 C21-C6 = C74-C21 = C75-C74 = C76-C75 = C77-C76 = C78-C77
 1.52 with sigma of 0.002
 C80-C78 = C79-C80
 1.52 with sigma of 0.002
 C82-C79 = C82-C81 = C81-C83
 1.52 with sigma of 0.002
 C84-C55 = C85-C84 = C86-C85 = C87-C86 = C88-C87
 1.52 with sigma of 0.002
 C89-C88
 1.52 with sigma of 0.002
 C90-C95 = C91-C95 = C96-C91 = C93-C96 = C92-C93 = C94-C92
 1.52 with sigma of 0.002
 C97-C90 = C98-C97 = C104-C98 = C99-C104 = C102-C99 = C102-C100 = C103-C100 =
 C101-C103
 1.52 with sigma of 0.002
 C55-C58
 2.52 with sigma of 0.005
 C56-C70
 2.52 with sigma of 0.005
 C70-C69
 2.52 with sigma of 0.005
 C59-C60
 2.52 with sigma of 0.005
 C57-C56
 2.52 with sigma of 0.005
 C58-C59
 2.52 with sigma of 0.005
 C60-C71
 2.52 with sigma of 0.005
 C57-C54
 2.52 with sigma of 0.005
 C62-C64
 2.52 with sigma of 0.005
 C65-C68
 2.52 with sigma of 0.005
 C66-C67
 2.52 with sigma of 0.005
 C63-C65
 2.52 with sigma of 0.005
 C64-C66
 2.52 with sigma of 0.005
 C61-C63
 2.52 with sigma of 0.005
 C68-C72
 2.52 with sigma of 0.005
 C61-C4
 2.52 with sigma of 0.005
 C27-C62
 2.52 with sigma of 0.005
 C67-C73
 2.52 with sigma of 0.005
 C75-C77
 2.52 with sigma of 0.005
 C6-C74
 2.52 with sigma of 0.005
 C76-C78
 2.52 with sigma of 0.005
 C21-C75
 2.52 with sigma of 0.005
 C74-C76
 2.52 with sigma of 0.005
 C78-C79
 2.52 with sigma of 0.005
 C77-C80
 2.52 with sigma of 0.005
 C82-C83
 2.52 with sigma of 0.005
 C79-C81
 2.52 with sigma of 0.005
 C80-C82
 2.52 with sigma of 0.005
 C85-C87
 2.52 with sigma of 0.005
 C86-C88
 2.52 with sigma of 0.005
 C84-C86
 2.52 with sigma of 0.005
 C55-C85
 2.52 with sigma of 0.005
 C89-C87
 2.52 with sigma of 0.005
 C93-C94
 2.52 with sigma of 0.005
 C91-C93
 2.52 with sigma of 0.005
 C96-C92
 2.52 with sigma of 0.005
 C95-C96
 2.52 with sigma of 0.005
 C90-C91
 2.52 with sigma of 0.005
 C104-C102
 2.52 with sigma of 0.005
 C102-C103
 2.52 with sigma of 0.005
 C99-C100
 2.52 with sigma of 0.005
 C90-C98
 2.52 with sigma of 0.005
 C100-C101
 2.52 with sigma of 0.005
 C97-C104
 2.52 with sigma of 0.005
 C98-C99
 2.52 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57
\\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65
\\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C73
\\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C78 \\sim C79 \\sim C80 \\sim C81
\\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89
\\sim C90 \\sim C91 \\sim C92 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97
\\sim C98 \\sim C99 \\sim C100 \\sim C101 \\sim C102 \\sim C103 \\sim C104:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C90 \\sim C95: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
5.a Riding coordinates:
 C71(H71A,H71B,H71C), C73(H73A,H73B,H73C), C83(H83A,H83B,H83C), C88(H88A,H88B),
  C89(H89A,H89B,H89C), C101(H10C,H10D,H10E)
5.b Ternary CH refined with riding coordinates:
 C55(H55), C90(H90)
5.c Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C27(H27A,H27B), C53(H53A,H53B), C54(H54A,H54B), C56(H56A,
 H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B),
 C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B),
  C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,
 H70B), C72(H72A,H72B), C74(H74A,H74B), C75(H75A,H75B), C76(H76A,H76B),
 C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C81(H81A,H81B),
  C82(H82A,H82B), C84(H84A,H84B), C85(H85A,H85B), C86(H86A,H86B), C87(H87A,
 H87B), C91(H91A,H91B), C92(H92A,H92B), C93(H93A,H93B), C95(H95A,H95B),
 C96(H96A,H96B), C97(H97A,H97B), C98(H98A,H98B), C99(H99A,H99B), C100(H10A,
 H10B), C102(H10F,H10G), C103(H10H,H10I), C104(H10J,H10K)
5.d Aromatic/amide H refined with riding coordinates:
 C24(H24), C26(H26), C28(H28), C31(H31), C38(H38), C43(H43), C46(H46), C49(H49)
5.e Idealised Me refined as rotating group:
 C94(H94A,H94B,H94C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              44194
_shelx_hkl_checksum              94648
_shelx_fab_checksum              59394
_olex2_submission_special_instructions 'No special instructions were received'