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_1564847
_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 Cl2 N8 O2 S5'
_chemical_formula_sum            'C90 H102 Br2 Cl2 N8 O2 S5'
_chemical_formula_weight         1718.81
_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             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                107.551(2)
_cell_angle_beta                 114.327(3)
_cell_angle_gamma                90.288(2)
_cell_formula_units_Z            2
_cell_length_a                   16.0896(6)
_cell_length_b                   17.7032(4)
_cell_length_c                   17.9514(5)
_cell_measurement_reflns_used    11399
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6910
_cell_measurement_theta_min      2.6070
_cell_volume                     4392.9(3)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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    -23.00  63.00   0.50    6.00    --   46.95 -61.00  73.00  172
  2  \w     34.00  75.00   0.50   16.00    --  103.25 -61.00  73.00   82
  3  \w     31.00 106.00   0.50   16.00    --  103.25 -94.00 150.00  150
  4  \w     37.00  87.00   0.50   16.00    --  103.25-125.00 150.00  100
  5  \w     31.00  94.00   0.50    6.00    --   46.95-125.00  90.00  126
  6  \w     50.00  99.00   0.50   16.00    --  103.25 -94.00   0.00   98
  7  \w     84.00 111.00   0.50   16.00    --  103.25-125.00  30.00   54
  8  \w     79.00 111.00   0.50   16.00    --  103.25-125.00 -90.00   64
  9  \w     53.00  81.00   0.50   16.00    --  103.25 -94.00-180.00   56
 10  \w     32.00  75.00   0.50   16.00    --  103.25-125.00-180.00   86
 11  \w     32.00 109.00   0.50   16.00    --  103.25 -77.00-180.00  154
 12  \w     49.00  86.00   0.50   16.00    --  103.25 -94.00 -60.00   74
 13  \w     31.00  87.00   0.50   16.00    --  103.25 -94.00 -30.00  112
 14  \w     33.00  98.00   0.50   16.00    --  103.25 -94.00  30.00  130
 15  \w     32.00 100.00   0.50   16.00    --  103.25 -94.00 -90.00  136
 16  \w     24.00  89.00   0.50    6.00    --   46.95-125.00 -60.00  130
 17  \w     94.00 168.00   0.50   16.00    --  103.25  30.00 -90.00  148
 18  \w    124.00 151.00   0.50   16.00    --  103.25  45.00-180.00   54
 19  \w     88.00 167.00   0.50   16.00    --  103.25  61.00-148.00  158
 20  \w    107.00 169.00   0.50   16.00    --  103.25  30.00 -60.00  124
 21  \w    107.00 145.00   0.50   16.00    --  103.25  61.00 -30.00   76
 22  \w     81.00 169.00   0.50   16.00    --  103.25  77.00  60.00  176
 23  \w     83.00 169.00   0.50   16.00    --  103.25  77.00 120.00  172
 24  \w     33.00 118.00   0.50    6.00    --   46.95  61.00-148.00  170
 25  \w    -67.00 -27.00   0.50   16.00    --  -99.00  61.00-148.00   80
 26  \w    -58.00  22.00   0.50    6.00    --  -46.95  61.00-148.00  160
 27  \w    -67.00 -26.00   0.50   16.00    --  -99.00 125.00-150.00   82
 28  \w    -83.00 -27.00   0.50   16.00    --  -99.00 144.00-112.36  112
 29  \w    -68.00 -27.00   0.50   16.00    --  -99.00  61.00  30.00   82
 30  \w    -70.00 -45.00   0.50   16.00    --  -99.00 125.00 120.00   50
 31  \w   -111.00 -33.00   0.50   16.00    --  -99.00 125.00  60.00  156
 32  \w   -112.00 -86.00   0.50   16.00    --  -99.00 125.00   0.00   52
 33  \w   -124.00 -94.00   0.50   16.00    --  -99.00 142.00  41.40   60
 34  \w   -112.00 -75.00   0.50   16.00    --  -99.00 125.00 120.00   74
 35  \w   -126.00-100.00   0.50   16.00    --  -99.00 144.00-112.36   52
 36  \w   -112.00 -81.00   0.50   16.00    --  -99.00 125.00-150.00   62
 37  \w   -116.00 -30.00   0.50    6.00    --  -46.95 -61.00  73.00  172
 38  \w   -103.00 -74.00   0.50    6.00    --  -46.95-125.00-150.00   58
 39  \w   -167.00 -86.00   0.50   16.00    --  -99.00 -47.00  37.55  162
 40  \w   -110.00 -83.00   0.50   16.00    --  -99.00 -61.00  73.00   54
 41  \w   -168.00-119.00   0.50   16.00    --  -99.00 -61.00  73.00   98
 42  \w   -160.00-113.00   0.50   16.00    --  -99.00 -46.00-179.24   94
;
_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      -0.0632195000
_diffrn_orient_matrix_UB_12      0.0524109000
_diffrn_orient_matrix_UB_13      -0.0466583000
_diffrn_orient_matrix_UB_21      -0.0824517000
_diffrn_orient_matrix_UB_22      -0.0405116000
_diffrn_orient_matrix_UB_23      0.0037973000
_diffrn_orient_matrix_UB_31      0.0222837000
_diffrn_orient_matrix_UB_32      0.0642704000
_diffrn_orient_matrix_UB_33      0.0882407000
_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  0.0927
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            58813
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        64.999
_diffrn_reflns_theta_max         64.999
_diffrn_reflns_theta_min         2.647
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54918
_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            'pinkish black'
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             1796
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.182
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1024
_refine_ls_number_reflns         14286
_refine_ls_number_restraints     876
_refine_ls_restrained_S_all      9.386
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.1141
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1800P)^2^+15.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2918
_refine_ls_wR_factor_ref         0.3188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8540
_reflns_number_total             14286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ee01832a2.cif
_cod_data_source_block           tx5189a
_cod_depositor_comments
'Adding full bibliography for 1564845--1564847.cif.'
_cod_database_code               1564847
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHNOSFClBr
_shelx_estimated_absorpt_t_max   0.564
_shelx_estimated_absorpt_t_min   0.564
_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
 C1AA-C47
 1.54 with sigma of 0.02
 C2-C1AA
 2.5 with sigma of 0.02
 C9-C11
 1.54 with sigma of 0.02
 C77-C67
 1.54 with sigma of 0.02
 C20-C02D
 1.54 with sigma of 0.02
 C77-C70
 1.54 with sigma of 0.02
 C70-C77
 1.54 with sigma of 0.02
 C70-C67
 2.5 with sigma of 0.02
 C19-C12
 2.5 with sigma of 0.02
 C19-C7
 1.54 with sigma of 0.02
 C026-C020 = C026-C4 = C026-C19
 1.54 with sigma of 0.02
 C19-C4
 1.54 with sigma of 0.02
 C7-C4
 2.5 with sigma of 0.02
 C12-C7
 1.54 with sigma of 0.01
 C3-C12
 1.54 with sigma of 0.01
 C7-C3
 2.7 with sigma of 0.02
 C8-C3
 1.54 with sigma of 0.02
 C8-C7
 3.5 with sigma of 0.02
 C15_$1-C12
 3 with sigma of 0.02
 C13-C8
 1.54 with sigma of 0.01
 C15-C12_$5
 4 with sigma of 0.02
 C3_$5-C15
 4 with sigma of 0.02
 N00B_$6-C027
 3.5 with sigma of 0.02
 C027-N00B_$6
 4 with sigma of 0.02
 C13-C10
 1.54 with sigma of 0.01
 C8-C13
 1.8 with sigma of 0.01
 C15-C2
 1.54 with sigma of 0.01
 C2-C15
 1.54 with sigma of 0.01
 C02L-C2
 1.54 with sigma of 0.01
 C2-C02L
 1.54 with sigma of 0.001
 C02L-C15
 2.5 with sigma of 0.01
 C15_$8-C3_$9
 2.5 with sigma of 0.02
 C47-C02L
 2.7 with sigma of 0.02
 C02L-C1AA
 1.54 with sigma of 0.02
 H12B_$1-H2A = C2_$1-C12
 2.7 with sigma of 0.02
 C12-C2_$1
 3 with sigma of 0.02
 C19-C3
 3.5 with sigma of 0.02
 C12_$5-C2
 3.9 with sigma of 0.02
 C15_$10-C8_$11
 3.9 with sigma of 0.02
 C4-C12
 3.9 with sigma of 0.02
 C010_$2-C15
 3.9 with sigma of 0.02
 C15-C8_$5
 3.9 with sigma of 0.02
 C15-C3_$5
 4.2 with sigma of 0.02
 C13_$5-C15
 4.2 with sigma of 0.02
 C016-C8_$6
 3 with sigma of 0.02
 C8_$6-C016
 4.2 with sigma of 0.02
 C00Z-C3_$6
 3.5 with sigma of 0.02
 C026-C19
 3.5 with sigma of 0.02
 C2_$1-C12
 4.2 with sigma of 0.02
 C2-C12_$5
 4.2 with sigma of 0.02
 C20-C1
 2.5 with sigma of 0.02
 C02I-C47_$3
 4.2 with sigma of 0.02
 C1-C6
 2.5 with sigma of 0.02
 C3-C8
 2 with sigma of 0.02
 C12-C15_$1
 3.9 with sigma of 0.02
 C15_$1-C3
 3.9 with sigma of 0.02
 C15-Br03_$11
 2.5 with sigma of 0.02
 C15_$4-Br03
 3 with sigma of 0.02
 C022-C47
 2.5 with sigma of 0.02
 Br1A-C00J
 1.8 with sigma of 0.001
 C00J-Cl5
 2.7 with sigma of 0.001
 C00K-Cl5
 1.8 with sigma of 0.001
 C00Y-Cl5
 2.7 with sigma of 0.001
 C11-C9
 1.54 with sigma of 0.01
 C9-C02I
 2.5 with sigma of 0.01
 C02I-C11
 1.54 with sigma of 0.01
 C01E-C026
 2.5 with sigma of 0.01
 C026-C4
 1.54 with sigma of 0.01
 C01E-C020
 1.54 with sigma of 0.01
 C020-C4
 2.5 with sigma of 0.01
 C020-C026
 1.54 with sigma of 0.01
 C3-C7
 2.5 with sigma of 0.01
 C47-C02I
 3.2 with sigma of 0.001
 C4-C02D_$7
 3.6 with sigma of 0.01
 C47_$3-C9
 3.8 with sigma of 0.01
3. Restrained planarity
 C00J, Cl5, C00Y, C00K
 with sigma of 0.01
4. Rigid bond restraints
 C77
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C026, C4, C19, C7, C12, C3, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C9, C11, C02I, C027, C022, C01K
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl12, Br03, C01T, C01U, Cl04, Br1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Br1A, Cl1B, Cl5, Br02
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
C01K \\sim C022 \\sim C027 \\sim C02I \\sim C11 \\sim C9: within 2A with sigma
of 0.001 and sigma for terminal atoms of 0.002 within 2A
Br03 \\sim Cl12 \\sim C01T \\sim C01U \\sim Cl04 \\sim Br1: within 2A with
sigma of 0.001 and sigma for terminal atoms of 0.002 within 2A
Br1A \\sim Cl1B \\sim Cl5 \\sim Br02: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
6. Others
 Fixed Sof: Br02(0.5) Br03(0.5) Cl04(0.5) Br1(0.5) Cl12(0.5) Cl5(0.5)
 Br1A(0.5) Cl1B(0.5)
7.a Ternary CH refined with riding coordinates:
 C01X(H01X), C022(H022)
7.b Secondary CH2 refined with riding coordinates:
 C018(H01A,H01B), C01E(H01C,H01D), C01K(H01E,H01F), C01O(H01G,H01H), C01V(H01I,
 H01J), C01W(H01K,H01L), C01Z(H01M,H01O), C020(H02A,H02B), C021(H02C,H02D),
 C023(H02E,H02F), C024(H02G,H02H), C026(H02I,H02J), C027(H02K,H02L), C02A(H02M,
 H02N), C02D(H02O,H02P), C02E(H02Q,H02R), C02I(H02S,H02T), C02K(H02U,H02V),
 C02L(H02W,H02X), C11(H11A,H11B), C1AA(H1AA,H1AB), C4AA(H4AA,H4AB), C47(H47A,
 H47B), C5(H5A,H5B), C1(H1A,H1B), C2(H2A,H2B), C67(H67A,H67B), C77(H77A,H77B),
 C20(H20A,H20B), C4(H4A,H4B), C3(H3A,H3B), C19(H19A,H19B), C7(H7A,H7B),
 C12(H12A,H12B), C17(H17A,H17B), C8(H8A,H8B), C13(H13A,H13B), C60(H60A,H60B)
7.c Aromatic/amide H refined with riding coordinates:
 C00Y(H00Y), C00Z(H00Z), C010(H010), C013(H013), C01N(H01N), C01S(H01S)
7.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C6(H6A,H6B,H6C), C15(H15A,H15B,H15C), C9(H9A,H9B,H9C),
 C70(H70A,H70B,H70C), C10(H10A,H10B,H10C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              42862
_shelx_fab_checksum              30478
_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 3.572
_oxdiff_exptl_absorpt_empirical_full_min 0.458