Non-fullerene acceptors with hetero-dihalogenated terminals induce significant difference in single crystallography and enable binary organic solar cells with 17.5% efficiency
Wang, Lai; An, Qiaoshi; Yan, Lu; Bai, Hai-Rui; Jiang, Mengyun; Mahmood, Asif; Yang, Can; Zhi, Hongfu; Wang, Jin-Liang; Energy & Environmental Science 15 (2022) 320–333; doi:10.1039/D1EE01832A

data_1564846
_publ_section_title
;
 Non-fullerene acceptors with hetero-dihalogenated terminals induce
 significant difference in single crystallography and enable binary
 organic solar cells with 17.5% efficiency
;
_journal_issue                   1
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              320
_journal_page_last               333
_journal_paper_doi               10.1039/D1EE01832A
_journal_volume                  15
_journal_year                    2022
_chemical_formula_moiety         'C90 H102 Br2 F2 N8 O2 S5'
_chemical_formula_sum            'C90 H102 Br2 F2 N8 O2 S5'
_chemical_formula_weight         1685.91
_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_creation_date             2021-08-05
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-08-06 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.898(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.7059(7)
_cell_length_b                   23.0515(7)
_cell_length_c                   31.3331(11)
_cell_measurement_reflns_used    13435
_cell_measurement_temperature    169.99(12)
_cell_measurement_theta_max      71.5770
_cell_measurement_theta_min      2.5650
_cell_volume                     18355.5(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -18.00  59.00   0.50    0.80    --   46.95 -72.00  14.00  154
  2  \w     67.00  93.00   0.50    5.00    --  103.25 -72.00  14.00   52
  3  \w     38.00  70.00   0.50    5.00    --  103.25 -61.00 -60.00   64
  4  \w     45.00  75.00   0.50    5.00    --  103.25 -61.00 -90.00   60
  5  \w     32.00  63.00   0.50    5.00    --  103.25 -72.00  14.00   62
  6  \w     31.00  57.00   0.50    5.00    --  103.25 -61.00  60.00   52
  7  \w     41.00  75.00   0.50    5.00    --  103.25 -61.00 150.00   68
  8  \w     98.00 138.00   0.50    5.00    --  103.25  45.00  60.00   80
  9  \w    113.00 154.00   0.50    5.00    --  103.25  45.00  90.00   82
 10  \w    135.00 161.00   0.50    5.00    --  103.25  72.00 144.00   52
 11  \w     45.00  95.00   0.50    0.80    --   46.95  72.00 144.00  100
 12  \w    -63.00  25.00   0.50    0.80    --  -46.95  72.00 144.00  176
 13  \w     55.00 104.00   0.50    5.00    --  103.25 -94.00-180.00   98
 14  \w     31.00  62.00   0.50    5.00    --  103.25 -61.00-180.00   62
 15  \w    -76.00 -50.00   0.50    0.80    --  -46.95 -72.00  14.00   52
 16  \w   -108.00 -75.00   0.50    0.80    --  -46.95-125.00 150.00   66
 17  \w   -168.00 -91.00   0.50    5.00    --  -99.00 -72.00  14.00  154
 18  \w   -166.00 -89.00   0.50    5.00    --  -99.00 -45.00 -90.00  154
 19  \w   -101.00 -74.00   0.50    0.80    --  -46.95-125.00-180.00   54
 20  \w    -53.00 -26.00   0.50    5.00    --  -99.00  61.00  60.00   54
 21  \w    -65.00 -29.00   0.50    5.00    --  -99.00  61.00 120.00   72
 22  \w    -85.00 -37.00   0.50    5.00    --  -99.00  72.00 144.00   96
 23  \w   -102.00 -27.00   0.50    5.00    --  -99.00  77.00 -30.00  150
 24  \w    -65.00 -35.00   0.50    5.00    --  -99.00  61.00 -60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0264739000
_diffrn_orient_matrix_UB_12      0.0099202000
_diffrn_orient_matrix_UB_13      -0.0505634000
_diffrn_orient_matrix_UB_21      0.0360913000
_diffrn_orient_matrix_UB_22      0.0526801000
_diffrn_orient_matrix_UB_23      0.0015054000
_diffrn_orient_matrix_UB_31      0.0409316000
_diffrn_orient_matrix_UB_32      -0.0398776000
_diffrn_orient_matrix_UB_33      -0.0104797000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            63311
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.380
_diffrn_reflns_theta_min         2.588
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull dark black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             7056
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.106
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1024
_refine_ls_number_reflns         18003
_refine_ls_number_restraints     442
_refine_ls_restrained_S_all      2.516
_refine_ls_R_factor_all          0.1987
_refine_ls_R_factor_gt           0.1623
_refine_ls_shift/su_max          0.072
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1800P)^2^+40.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4128
_refine_ls_wR_factor_ref         0.4474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8292
_reflns_number_total             18003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ee01832a2.cif
_cod_data_source_block           tx5056
_cod_depositor_comments
'Adding full bibliography for 1564845--1564847.cif.'
_cod_database_code               1564846
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHNOClBrS
_shelx_estimated_absorpt_t_max   0.510
_shelx_estimated_absorpt_t_min   0.283
_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
 C01A-C00O
 1.54 with sigma of 0.001
 C00O-C01Q
 1.54 with sigma of 0.001
 C01Q-C02C
 1.54 with sigma of 0.001
 C02C-C02A
 1.54 with sigma of 0.001
 C02A-C21
 1.54 with sigma of 0.001
 C00O-C01Y
 1.54 with sigma of 0.001
 C01Y-C021
 1.54 with sigma of 0.001
 C021-C16
 1.54 with sigma of 0.001
 C16-C13
 1.54 with sigma of 0.001
 C13-C0AA
 1.54 with sigma of 0.001
 C0AA-C6
 1.54 with sigma of 0.001
 C01D-C00S
 1.54 with sigma of 0.001
 C024-C01D
 1.54 with sigma of 0.001
 C028-C024
 1.54 with sigma of 0.001
 C028-C14
 1.54 with sigma of 0.001
 C14-C33
 1.54 with sigma of 0.001
 C01D-C01Z
 1.54 with sigma of 0.001
 C01Z-C025
 1.54 with sigma of 0.001
 C025-C027
 1.54 with sigma of 0.001
 C027-C25
 1.54 with sigma of 0.001
 C25-C31
 1.54 with sigma of 0.001
 C01X-C029
 1.54 with sigma of 0.001
 C029-C26
 1.54 with sigma of 0.001
 C26-C58
 1.54 with sigma of 0.001
 C58-C40
 1.54 with sigma of 0.001
 C40-C10
 1.54 with sigma of 0.001
 C10-C11
 1.54 with sigma of 0.001
 C01C-C022
 1.54 with sigma of 0.001
 C022-C023
 1.54 with sigma of 0.001
 C023-C026
 1.54 with sigma of 0.001
 C026-C02D
 1.54 with sigma of 0.001
 C02D-C27
 1.54 with sigma of 0.001
 C27-C18
 1.54 with sigma of 0.001
 C46-C34
 1.54 with sigma of 0.001
 C34-C23
 1.54 with sigma of 0.001
 C5-C23
 1.54 with sigma of 0.001
 C34-C5
 2.8 with sigma of 0.02
 C11-C70
 1.54 with sigma of 0.001
 C70-C3
 1.54 with sigma of 0.001
 C3-C11
 2.8 with sigma of 0.02
 C1AA-C3
 1.54 with sigma of 0.001
 C2-C1AA
 1.54 with sigma of 0.001
 C3-C3_$1
 3.8 with sigma of 0.02
 C027-C31
 2.8 with sigma of 0.02
 C11-C40
 2.8 with sigma of 0.02
 C58-C01X
 3.2 with sigma of 0.02
 C70_$1-C70
 3.8 with sigma of 0.02
 C3_$1-C11
 3.8 with sigma of 0.02
 C3-C11_$1
 3.8 with sigma of 0.02
 C25_$2-C10
 3.8 with sigma of 0.02
 C46-C58_$3
 3.8 with sigma of 0.02
 C33_$4-C6
 3.8 with sigma of 0.02
 C10-C70
 2.8 with sigma of 0.02
 C22-C31
 1.54 with sigma of 0.001
 C22-C25
 2.5 with sigma of 0.02
 C027-C22
 2.9 with sigma of 0.02
 C01P-Br3
 1.8 with sigma of 0.01
 C46-C23
 2.5 with sigma of 0.01
 C40_$3-C46
 3.5 with sigma of 0.001
 C22-C00S_$4
 3.3 with sigma of 0.01
 C46_$5-C40
 3.8 with sigma of 0.001
 C46-C40_$3
 3.8 with sigma of 0.001
 C01T-Br2A
 1.8 with sigma of 0.001
 Br00-C020 \\sim F-C020
 with sigma of 0.02
3. Rigid bond restraints
 C01X, C029, C26, C58, C10, C11, C40
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C01C, C022, C023, C026, C02D, C18, C27, C46, C23, C34, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00S, C01D, C01Z, C024, C025, C027, C028, C14, C25, C31, C33
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00O, C01Q, C01Y, C02A, C02C, C21, C6, C0AA, C13, C021, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C34, C23, C46
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2, C1AA, C3, C70, C11, C10, C40, C58, C26, C029, C01X
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C22, C31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C31, C22, C25, C025, C027, C01Z, C01D
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C01D, C01Z, C025, C027, C25, C31, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C01X, C029, C26, C58, C40, C10, C11, C70, C3, C1AA, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C01X, C029, C26, C58, C40, C01B, C10, C11, C70, C3, C1AA, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00F, S003, C00N, C01F
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C01B, C00F, C01F, C00N
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4. Uiso/Uaniso restraints and constraints
C01C \\sim C022 \\sim C023 \\sim C026 \\sim C02D \\sim C18 \\sim C27 \\sim C46
\\sim C23 \\sim C34 \\sim C5: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C01X \\sim C029 \\sim C26 \\sim C58 \\sim C10 \\sim C11 \\sim C40: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C00O \\sim C01Q \\sim C01Y \\sim C021 \\sim C02A \\sim C02C \\sim C13 \\sim C16
\\sim C21 \\sim C6 \\sim C0AA \\sim C01A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C00S \\sim C01D \\sim C01Z \\sim C024 \\sim C025 \\sim C027 \\sim C028 \\sim
C14 \\sim C25 \\sim C31 \\sim C33: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C46 \\sim C23 \\sim C34 \\sim C5: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C2 \\sim C1AA \\sim C3 \\sim C70 \\sim C11 \\sim C10 \\sim C40 \\sim C58 \\sim
C26 \\sim C029 \\sim C01X: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C22 \\sim C31: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C01D \\sim C01Z \\sim C025 \\sim C027 \\sim C25 \\sim C31 \\sim C22: within 2A
with sigma of 0.001 and sigma for terminal atoms of 0.002 within 2A
C01X \\sim C029 \\sim C26 \\sim C58 \\sim C40 \\sim C10 \\sim C11 \\sim C70
\\sim C3 \\sim C1AA \\sim C2: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
C2 \\sim C1AA \\sim C3 \\sim C11 \\sim C70 \\sim C10 \\sim C40 \\sim C58 \\sim
C26 \\sim C01X \\sim C029 \\sim C01B: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
C00F \\sim S003 \\sim C00N \\sim C01F: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
C00F \\sim C01B \\sim C01F \\sim C00N: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
5. Others
 Fixed Sof: Br00(0.75) Br1(0.75) F009(0.75) F2(0.75) Br3(0.25) F(0.25)
 F23(0.25) Br2A(0.25)
6.a Ternary CH refined with riding coordinates:
 C00O(H00O), C01D(H01E)
6.b Secondary CH2 refined with riding coordinates:
 C00S(H00A,H00B), C01A(H01A,H01B), C01C(H01C,H01D), C01Q(H01F,H01G), C01X(H01H,
 H01I), C01Y(H01J,H01L), C01Z(H01M,H01O), C021(H02A,H02B), C022(H02C,H02D),
 C023(H02E,H02F), C024(H02G,H02H), C025(H02I,H02J), C026(H02K,H02L), C027(H02M,
 H02N), C028(H02O,H02P), C029(H02Q,H02R), C02A(H02S,H02T), C02C(H02U,H02V),
 C02D(H02W,H02X), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C18(H18A,
 H18B), C25(H25A,H25B), C27(H27A,H27B), C31(H31A,H31B), C46(H46A,H46B),
 C23(H23A,H23B), C26(H26A,H26B), C58(H58A,H58B), C10(H10A,H10B), C11(H11A,H11B),
  C0AA(H0AA,H0AB), C40(H40A,H40B), C34(H34A,H34B), C70(H70A,H70B), C3(H3A,H3B),
 C1AA(H1AA,H1AB)
6.c Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00U(H00U), C018(H018), C01K(H01K), C01N(H01N), C01W(H01W)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C33(H33A,H33B,H33C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C),
 C2(H2A,H2B,H2C), C22(H22A,H22B,H22C)
;
_smtbx_masks_void_probe_radius   0.8
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              35529
_shelx_fab_checksum              71255
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.910
_oxdiff_exptl_absorpt_empirical_full_min 0.541