Asymmetric side-chain substitution enables a 3D network acceptor with hydrogen bond assisted crystal packing and enhanced electronic coupling for efficient organic solar cells
Luo, Zhenghui; Gao, Yuan; Lai, Hanjian; Li, Yuxiang; Wu, Ziang; Chen, Zhanxiang; Sun, Rui; Ren, Jiaqi; Zhang, Cai’e; He, Feng; Woo, HanYoung; Min, Jie; Yang, Chuluo; Energy & Environmental Science 15 (2022) 4601–4611; doi:10.1039/D2EE01848A

data_1567670
_publ_section_title
;
 Asymmetric side-chain substitution enables a 3D network acceptor with
 hydrogen bond assisted crystal packing and enhanced electronic coupling
 for efficient organic solar cells
;
_journal_issue                   11
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              4601
_journal_page_last               4611
_journal_paper_doi               10.1039/D2EE01848A
_journal_volume                  15
_journal_year                    2022
_chemical_formula_moiety         '1.008(C60 H10 F4 N8 O2 S5)'
_chemical_formula_sum            'C58 H44 F0.5 N16 O4.5 S5'
_chemical_formula_weight         1206.89
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2bzdmc
_audit_creation_date             2022-02-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-22 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                70.475(7)
_cell_angle_beta                 86.756(7)
_cell_angle_gamma                80.476(7)
_cell_formula_units_Z            4
_cell_length_a                   13.457(2)
_cell_length_b                   23.140(4)
_cell_length_c                   30.127(5)
_cell_measurement_reflns_used    9422
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50.80
_cell_measurement_theta_min      2.96
_cell_volume                     8720(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.894
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.894
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            88338
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        51.679
_diffrn_reflns_theta_max         51.679
_diffrn_reflns_theta_min         2.051
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  0.7501
_exptl_absorpt_correction_T_min  0.4859
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1509 before and 0.1100 after correction.
The Ratio of minimum to maximum transmission is 0.6478.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    0.919
_exptl_crystal_description       needle
_exptl_crystal_F_000             2498
_refine_diff_density_max         1.187
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1231
_refine_ls_number_reflns         17206
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.2085
_refine_ls_R_factor_gt           0.1764
_refine_ls_shift/su_max          0.000
_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^+120.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4153
_refine_ls_wR_factor_ref         0.4480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12666
_reflns_number_total             17206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ee01848a2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 1567669--1567670.cif.'
_cod_original_formula_sum        'C58 H44 F0.50 N16 O4.50 S5'
_cod_database_code               1567670
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C79-C78
 1.4 with sigma of 0.02
 C81-C82
 1.4 with sigma of 0.02
 C77-C75
 1.4 with sigma of 0.02
 C83-C84 = C83-C82 = C81-C82 = C81-C80 = C79-C80
 1.39 with sigma of 0.02
 N15-C85
 1.2 with sigma of 0.02
 C85-C119
 1.54 with sigma of 0.02
 F3AA-C82 = F2AA-C81 = F1AA-C15 = F2-C16
 1.38 with sigma of 0.02
 C75-C74
 1.4 with sigma of 0.02
 C72-C10
 1.39 with sigma of 0.02
 C76-C119
 1.39 with sigma of 0.02
 C120-C119
 1.54 with sigma of 0.02
 C85-C119 = C120-C119
 1.4 with sigma of 0.02
 N16-C120
 1.15 with sigma of 0.02
 O4-C78
 1.2 with sigma of 0.02
 F3AA-C82 = F2AA-C81
 1.35 with sigma of 0.02
 C57-C53
 1.543 with sigma of 0.02
 C18-C117 = C1A-C117
 1.45 with sigma of 0.02
 C59-C58
 1.47 with sigma of 0.02
 C35-C34 = C9-C34
 1.54 with sigma of 0.02
 C9-C21 = C9-C36
 1.38 with sigma of 0.02
 C9-C21
 1.38 with sigma of 0.1
 N8-C59
 1.15 with sigma of 0.02
 N3-C7 = N3-C1
 1.38 with sigma of 0.02
 C84-C82
 2.33 with sigma of 0.04
 C79-C81
 2.33 with sigma of 0.04
 C83-C81
 2.33 with sigma of 0.04
 C84-C81
 2.78 with sigma of 0.04
 C120-C84
 3 with sigma of 0.04
 C85-C77
 3 with sigma of 0.04
 C120-C83
 3 with sigma of 0.04
 C76-C120
 2.46 with sigma of 0.04
 C14-F1AA
 2.3 with sigma of 0.04
 C58-N8
 2.7 with sigma of 0.04
3. Rigid bond restraints
 C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C103, C104
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C80 \\sim C83 \\sim C79 \\sim C81 \\sim C82 \\sim C84: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C120 \\sim C85 \\sim N15 \\sim C119 \\sim C76: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C120 \\sim N16: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C119 \\sim N16: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C51 \\sim C56 \\sim C55 \\sim C54 \\sim C53 \\sim C52 \\sim C50: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C99 \\sim C104 \\sim C103 \\sim C102 \\sim C101 \\sim C100 \\sim C98: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(F2AA) \\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(F3AA)
\\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C79) \\sim Ueq,
Uanis(C78) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C76) \\sim Ueq, Uanis(C75)
\\sim Ueq, Uanis(C119) \\sim Ueq, Uanis(C120) \\sim Ueq, Uanis(N16) \\sim Ueq,
Uanis(N15) \\sim Ueq, Uanis(C85) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.02
Uanis(N1) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C58) \\sim Ueq, Uanis(C59)
\\sim Ueq, Uanis(N8) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1AA) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(N11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C73)
\\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.05 and sigma for terminal
atoms of 0.1
Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C29) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C65) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C59) \\sim Ueq, Uanis(N8) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(N1)
\\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
5.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C20(H20), C26(H26), C28(H28), C31(H31), C52(H52),
 C54(H54), C55(H55), C56(H56), C61(H61), C64(H64), C68(H68), C75(H75), C80(H80),
  C83(H83), C100(H100), C102(H102), C103(H103), C104(H104)
5.b Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C12(C14,C15,C16,C17,C18), C28(C29,C30,C31,C32,C33),
 C51(C52,C53,C54,C55,C56), C60(C61,C62,C63,C64,C65), C79(C80,C81,C82,C83,C84),
 C86(C87,C88,C89,C90,C91), C99(C100,C101,C102,C103,C104)
;
_shelx_res_checksum              18943
_shelx_fab_checksum              96903
_olex2_submission_special_instructions 'No special instructions were received'