Enhanced crystal network and charge transfer of non-fused ring electron acceptors via interchain interaction for efficient and stable organic solar cells
Ye, Shounuan; Chen, Tianyi; Yu, Jinyang; Wang, Shanlu; Li, Shuixing; Wang, Jingxi; Fu, Yuang; Zhu, Yuxuan; Wang, Mengting; Lu, Xinhui; Ma, Zaifei; Li, Chang-Zhi; Shi, Minmin; Chen, Hongzheng; Energy & Environmental Science 17 (2024) 5137–5146; doi:10.1039/D4EE02027H

data_1571805
_publ_section_title
;
 Enhanced crystal network and charge transfer of non-fused ring electron
 acceptors via interchain interaction for efficient and stable organic
 solar cells
;
_journal_issue                   14
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              5137
_journal_page_last               5146
_journal_paper_doi               10.1039/D4EE02027H
_journal_volume                  17
_journal_year                    2024
_chemical_formula_moiety         'C84 H75 F4 N4 O6 S6, C42 H38 F2 N2 O3 S3'
_chemical_formula_sum            'C126 H113 F6 N6 O9 S9'
_chemical_formula_weight         2257.76
_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_creation_date             2024-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2024-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                98.961(5)
_cell_angle_beta                 96.362(4)
_cell_angle_gamma                98.914(5)
_cell_formula_units_Z            2
_cell_length_a                   15.5739(12)
_cell_length_b                   18.8499(15)
_cell_length_c                   20.1648(13)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.390
_cell_measurement_theta_min      2.900
_cell_volume                     5721.3(7)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1159
_diffrn_reflns_av_unetI/netI     0.2119
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            63824
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.240
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.199
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1369 before and 0.0915 after correction.
The Ratio of minimum to maximum transmission is 0.4706.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             2362
_refine_diff_density_max         1.157
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1408
_refine_ls_number_reflns         20079
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.2413
_refine_ls_R_factor_gt           0.1847
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4266
_refine_ls_wR_factor_ref         0.4694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10035
_reflns_number_total             20079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ee02027h2.cif
_cod_data_source_block           cu_20240308ysn_h_0m_a
_cod_depositor_comments
'Adding full bibliography for 1571803--1571805.cif.'
_cod_database_code               1571805
_shelx_shelxl_version_number     2016/6
_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
 C18-C8
 1.5 with sigma of 0.02
 C8-C5 = C8-C10
 1.41 with sigma of 0.02
 N4-C5 = N11-C10
 1.1 with sigma of 0.02
 C01U-N01C = C8-N11
 2.5 with sigma of 0.02
 C8-N4
 2.7 with sigma of 0.02
 C01Y-C01M = C8-C18
 1.33 with sigma of 0.02
 C18-C03Z = C18-C03C
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(N11) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C03C) \\sim Ueq,
Uanis(C03U) \\sim Ueq, Uanis(C03Y) \\sim Ueq, Uanis(C03Z) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C03W) \\sim Ueq, Uanis(C03V) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(F19) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(O17) \\sim Ueq, Uanis(C02X)
\\sim Ueq, Uanis(C02I) \\sim Ueq, Uanis(C034) \\sim Ueq, Uanis(C02T) \\sim Ueq,
Uanis(C01S) \\sim Ueq, Uanis(C021) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F20) \\sim Ueq, Uanis(F19) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C047) \\sim Ueq, Uanis(C048) \\sim Ueq, Uanis(C03P) \\sim Ueq,
Uanis(C044) \\sim Ueq, Uanis(C045) \\sim Ueq, Uanis(C042) \\sim Ueq,
Uanis(C040) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(O17) \\sim Ueq,
Uanis(C03U) \\sim Ueq, Uanis(C03Y) \\sim Ueq, Uanis(C03Z) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C03W) \\sim Ueq, Uanis(C03V) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C03C) \\sim Ueq, Uanis(C02X) \\sim Ueq, Uanis(C02I) \\sim Ueq,
Uanis(C02T) \\sim Ueq, Uanis(C034) \\sim Ueq, Uanis(C03D) \\sim Ueq,
Uanis(C02P) \\sim Ueq, Uanis(C03X) \\sim Ueq, Uanis(C043) \\sim Ueq,
Uanis(C041) \\sim Ueq, Uanis(C03Q) \\sim Ueq, Uanis(C046) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C01Z(H01Z), C02K(H02V), C02L(H02L), C03L(H03Q), C03P(H03U), C040(H040)
4.b Secondary CH2 refined with riding coordinates:
 C01L(H01A,H01B), C023(H02N,H02P), C025(H02A,H02B), C029(H02T,H02U), C02J(H02C,
 H02D), C02M(H02,H), C02P(H02I,H02J), C02V(H02K,H02M), C031(H03Y,HA), C032(H03A,
 H03B), C033(H03C,H03D), C034(H03E,H03F), C035(H03G,H03H), C03D(H03L,H03M),
 C03E(H03,HD), C03N(H4AA,HI), C03R(H6AA,HL), C03X(H03W,H03X), C041(H04A,H04B),
 C043(H04F,H04G)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C016(H016), C16(H16), C15(H15), C01B(H01C), C01E(H01E),
 C01W(H01W), C026(H026), C26(H26), C02G(H02G), C02O(H02O), C02W(H02W),
 C02X(H02X), C02Y(H02Y), C02Z(H02Z), C030(H030), C036(H036), C039(H039),
 C03F(H0AA), C03K(H3AA), C03Q(H03V)
4.d Fitted hexagon refined as free rotating group:
 C16(C03W,C03V,C15,C03Y,C03Z)
4.e Idealised Me refined as rotating group:
 C027(H02Q,H02R,H02S), C02N(H02E,H02F,H02H), C03A(H03Z,HB,HC), C03B(H03I,H03J,
 H03K), C03H(H1AA,HE,HF), C03I(H2AA,HG,HH), C03J(H03N,H03O,H03P), C03M(H03R,
 H03S,H03T), C03O(H5AA,HJ,HK), C042(H04C,H04D,H04E), C044(H04H,H04I,H04J),
 C045(H04K,H04L,H04M), C046(H04N,H04O,H04P), C047(H04Q,H04R,H04S), C048(H04T,
 H04U,H04V)
;
_shelx_res_checksum              94679
_shelx_hkl_checksum              15028
_olex2_submission_special_instructions 'No special instructions were received'