Medium Band-Gap Non-fullerene Acceptors Based on Benzothiophene Donor Moiety Enabling High-Performance Indoor Organic Photovoltaics
Li, Xiaojun; Luo, Siwei; sun, huiliang; Liu, Tao; Sung, Herman H-Y.; Yu, Han; Xiao, Yiqun; Bai, Fujin; Pan, Mingao; Lu, Xinhui; Williams, Ian Duncan; Guo, Xugang; Li, Yongfang; Yan, He; Energy & Environmental Science  (2021) –; doi:10.1039/D1EE00687H

data_1564073
_publ_section_title
;
 Medium Band-Gap Non-fullerene Acceptors Based on Benzothiophene Donor
 Moiety Enabling High-Performance Indoor Organic Photovoltaics
;
_journal_name_full               'Energy &amp; Environmental Science'
_journal_paper_doi               10.1039/D1EE00687H
_journal_year                    2021
_chemical_formula_moiety         'C80 H74 F4 N8 O2 S3'
_chemical_formula_sum            'C80 H74 F4 N8 O2 S3'
_chemical_formula_weight         1351.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-12-14
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-08 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.7559(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.93013(9)
_cell_length_b                   33.0819(3)
_cell_length_c                   23.3061(3)
_cell_measurement_reflns_used    33385
_cell_measurement_temperature    173.0(1)
_cell_measurement_theta_max      76.7930
_cell_measurement_theta_min      3.8040
_cell_volume                     7629.87(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-beta (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_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     83.00 110.00   0.60   15.00    --  113.00  61.00 -60.00   45
  2  \w   -111.00 -21.00   0.60    3.00    --  -39.95 -37.00 -90.00  150
  3  \w    -86.00  -8.00   0.60    3.00    --  -39.95 125.00 -90.00  130
  4  \w   -114.00 -21.00   0.60    3.00    --  -39.95 -37.00 120.00  155
  5  \w    -65.00  31.00   0.60    3.00    --  -39.95  37.00  90.00  160
  6  \w      3.00  29.40   0.60    3.00    --   39.95  88.00 -50.48   44
  7  \w      3.00  30.00   0.60    3.00    --   39.95  88.00  64.27   45
  8  \w    -36.00  50.40   0.60    3.00    --   39.95 -37.00-150.00  144
  9  \w     10.00  46.00   0.60    3.00    --   39.95  57.00 150.00   60
 10  \w     11.00  51.20   0.60    3.00    --   39.95  57.00   0.00   67
 11  \w     14.00  83.00   0.60    3.00    --   39.95  57.00-120.00  115
 12  \w      2.00  27.20   0.60    3.00    --   39.95  89.00  34.81   42
 13  \w     58.00 103.60   0.60    3.00    --   39.95  57.00   0.00   76
 14  \w     48.00  90.00   0.60    3.00    --   39.95-125.00-150.00   70
 15  \w      3.00  30.00   0.60    3.00    --   39.95  87.00-178.82   45
 16  \w      4.00  29.20   0.60    3.00    --   39.95  89.00 -94.29   42
 17  \w     47.00  71.60   0.60    3.00    --   39.95-125.00  90.00   41
 18  \w    -36.00  54.00   0.60    3.00    --   39.95 -37.00 120.00  150
 19  \w     48.00  87.00   0.60    3.00    --   39.95  57.00  60.00   65
 20  \w     65.00 131.60   0.60   15.00    --  113.00 178.00   0.00  111
 21  \w    140.00 176.60   0.60   15.00    --  113.00  68.00-137.68   61
 22  \w     83.00 110.00   0.60   15.00    --  113.00  61.00  30.00   45
 23  \w     83.00 110.00   0.60   15.00    --  113.00  61.00 -30.00   45
 24  \w     85.00 121.00   0.60   15.00    --  113.00  45.00 -90.00   60
 25  \w     36.00 105.00   0.60   15.00    --  113.00 -94.00  60.00  115
 26  \w    127.00 174.40   0.60   15.00    --  113.00  61.00  30.00   79
 27  \w     83.00 110.00   0.60   15.00    --  113.00  61.00  90.00   45
 28  \w    111.00 176.40   0.60   15.00    --  113.00  61.00  90.00  109
 29  \w     81.00 108.00   0.60   15.00    --  113.00  68.00-137.68   45
 30  \w    123.00 177.00   0.60   15.00    --  113.00  61.00 -60.00   90
 31  \w     83.00 108.80   0.60   15.00    --  113.00  61.00 -98.39   43
 32  \w    139.00 169.60   0.60   15.00    --  113.00  45.00 120.00   51
 33  \w     88.00 112.60   0.60   15.00    --  113.00  45.00   0.00   41
 34  \w     85.00 133.00   0.60   15.00    --  113.00  45.00 120.00   80
 35  \w    121.00 177.40   0.60   15.00    --  113.00  61.00   0.00   94
 36  \w     83.00 175.40   0.60   15.00    --  113.00  61.00 150.00  154
 37  \w     83.00 116.60   0.60   15.00    --  113.00  61.00   0.00   56
 38  \w     82.00 107.80   0.60   15.00    --  113.00  64.00 139.53   43
 39  \w     86.00 113.00   0.60   15.00    --  113.00  45.00  30.00   45
 40  \w     85.00 112.00   0.60   15.00    --  113.00  45.00 -30.00   45
 41  \w     83.00 122.60   0.60   15.00    --  113.00  61.00 -90.00   66
 42  \w    124.00 154.00   0.60   15.00    --  113.00  61.00 -90.00   50
 43  \w     85.00 136.60   0.60   15.00    --  113.00  45.00 -60.00   86
 44  \w     84.00 108.60   0.60   15.00    --  113.00  61.00 120.00   41
 45  \w     83.00 108.80   0.60   15.00    --  113.00  61.00-180.00   43
 46  \w     85.00 113.80   0.60   15.00    --  113.00  45.00  90.00   48
 47  \w     85.00 112.00   0.60   15.00    --  113.00  45.00-150.00   45
 48  \w    113.00 176.00   0.60   15.00    --  113.00 111.00 -60.00  105
 49  \w     83.00 110.00   0.60   15.00    --  113.00  61.00  60.00   45
 50  \w     37.00 107.80   0.60   15.00    --  113.00-111.00-120.00  118
 51  \w     30.00 105.60   0.60   15.00    --  113.00 -94.00   0.00  126
 52  \w     83.00 110.00   0.60   15.00    --  113.00  61.00-120.00   45
 53  \w     83.00 170.00   0.60   15.00    --  113.00  61.00-150.00  145
 54  \w     85.00 113.80   0.60   15.00    --  113.00  45.00  60.00   48
 55  \w     40.00 107.80   0.60   15.00    --  113.00-111.00 -30.00  113
 56  \w     35.00 107.60   0.60   15.00    --  113.00-111.00 150.00  121
 57  \w     83.00 175.40   0.60   15.00    --  113.00  59.00 168.24  154
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1501587000
_diffrn_orient_matrix_UB_12      0.0033851000
_diffrn_orient_matrix_UB_13      -0.0220430000
_diffrn_orient_matrix_UB_21      0.0038998000
_diffrn_orient_matrix_UB_22      0.0457191000
_diffrn_orient_matrix_UB_23      0.0126047000
_diffrn_orient_matrix_UB_31      0.0408183000
_diffrn_orient_matrix_UB_32      0.0082359000
_diffrn_orient_matrix_UB_33      -0.0612717000
_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  0.0426
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56007
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         81.931
_diffrn_reflns_theta_min         3.806
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       plate
_exptl_crystal_F_000             2840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         8033
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0516
_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^)+(0.1099P)^2^+5.0856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7130
_reflns_number_total             8033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ee00687h2.cif
_cod_data_source_block           lixj1d_173k
_cod_original_cell_volume        7629.88(13)
_cod_database_code               1564073
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.610
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C44-C45A = C46A-C45A = C46A-C47A = C47A-C48A
 1.52 with sigma of 0.02
 C44-C45 = C46-C45 = C47-C46 = C48-C47
 1.52 with sigma of 0.02
 C30-C31 = C35-C36 = C36-C37 = C38-C37 = C37A-C38A = C37A-C36
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C48A) \\sim Ueq, Uanis(C47A) \\sim Ueq: with sigma of 0.008 and sigma for
terminal atoms of 0.02
Uanis(C36) \\sim Ueq, Uanis(C38A) \\sim Ueq, Uanis(C46A) \\sim Ueq: with sigma
of 0.008 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C43, C44, C45, C46, C47, C48
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C43, C44, C45A, C46A, C47A, C48A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C34, C35, C36, C37, C38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C35, C36, C37A, C38A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: H36A(0.25) H36B(0.25) H36C(0.25) H36D(0.25) H44A(0.35) H44B(0.35)
 H44C(0.65) H44D(0.65) C37(0.27) H37A(0.27) H37B(0.27) C38(0.27) H38A(0.27)
 H38B(0.27) H38C(0.27) C45(0.35) H45A(0.35) H45B(0.35) C46(0.35) H46A(0.35)
 H46B(0.35) C47(0.25) H47A(0.25) H47B(0.25) C48(0.25) H48A(0.25) H48B(0.25)
 H48C(0.25) C37A(0.23) H37C(0.23) H37D(0.23) C38A(0.23) H38D(0.23) H38E(0.23)
 H38F(0.23) C45A(0.65) H45C(0.65) H45D(0.65) C46A(0.65) H46C(0.65) H46D(0.65)
 C47A(0.25) H47C(0.25) H47D(0.25) C48A(0.25) H48D(0.25) H48E(0.25) H48F(0.25)
6.a Ternary CH refined with riding coordinates:
 C30(H30)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,
 H34B), C35(H35A,H35B), C36(H36A,H36B), C36(H36C,H36D), C41(H41A,H41B),
 C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C44(H44C,H44D), C37(H37A,H37B),
  C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C37A(H37C,H37D), C45A(H45C,
 H45D), C46A(H46C,H46D), C47A(H47C,H47D)
6.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C22(H22), C25(H25)
6.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C48(H48A,H48B,H48C), C38A(H38D,H38E,H38F), C48A(H48D,
 H48E,H48F)
;
_shelx_res_checksum              28318
_shelx_hkl_checksum              27462
_olex2_date_sample_data_collection 2020-12-04
_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 3.134
_oxdiff_exptl_absorpt_empirical_full_min 0.391