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_1567669
_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         'C74 H40 F4 N8 O2 S5, O'
_chemical_formula_sum            'C74 H44 F4 N8 O3 S5'
_chemical_formula_weight         1329.47
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2bzdlb
_audit_creation_date             2022-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-22 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.688(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.7933(13)
_cell_length_b                   57.270(3)
_cell_length_c                   13.4957(7)
_cell_measurement_reflns_used    9287
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.99
_cell_measurement_theta_min      4.56
_cell_volume                     17314.8(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       63
_diffrn_reflns_limit_k_min       -63
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            93113
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        58.983
_diffrn_reflns_theta_max         58.983
_diffrn_reflns_theta_min         3.041
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.655
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.5579
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1210 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.7423.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.020
_exptl_crystal_description       needle
_exptl_crystal_F_000             5472
_refine_diff_density_max         1.863
_refine_diff_density_min         -0.974
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     805
_refine_ls_number_reflns         12411
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.1201
_refine_ls_shift/su_max          0.001
_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^+100.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3265
_refine_ls_wR_factor_ref         0.3405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10781
_reflns_number_total             12411
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ee01848a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1567669--1567670.cif.'
_cod_original_cell_volume        17314.9(16)
_cod_database_code               1567669
_shelx_shelxl_version_number     2017/1
_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
 C67-C58 = C58-C48 = C64-C59 = C59-C48 = C66-C64 = C66-C65
 1.54 with sigma of 0.02
 C69-C36 = C69-C68
 1.54 with sigma of 0.02
 C74-C72 = C74-C70 = C68-C70 = C69-C68 = C71-C69 = C73-C71
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C74 \\sim N2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C69) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C67) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C74) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C68) = Uanis(C70) = Uanis(C74) = Uanis(C72)
Uanis(C58) = Uanis(C67)
4.a Ternary CH refined with riding coordinates:
 C48(H48), C69(H69)
4.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C58(H58A,H58B), C59(H59A,H59B), C64(H64A,H64B), C66(H66A,
 H66B), C68(H68A,H68B), C70(H70A,H70B), C71(H71A,H71B), C74(H74A,H74B)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C18(H18), C21(H21), C23(H23), C30(H30), C42(H42), C45(H45),
 C47(H47), C50(H50), C51(H51), C52(H52), C57(H57), C61(H61), C62(H62)
4.d Idealised Me refined as rotating group:
 C65(H65A,H65B,H65C), C72(H72A,H72B,H72C)
;
_shelx_res_checksum              68815
_shelx_fab_checksum              28888
_olex2_submission_special_instructions 'No special instructions were received'